


Kinktober 2018: The Kinkening

by Vexatious



Category: Undertale (Video Game)
Genre: 69 (Sex Position), Anal Fingering, Anal Fisting, Anal Plug, Anal Sex, Angry Sex, Aphrodisiacs, Begging, Biting, Blood and Injury, Blood and Violence, Bodily Harm/Injury (Dislocation), Body Worship, Bondage, Breast Fucking, Breast Worship, Breeding, Bukkake, Burnplay, Choking, Cock Rings, Cock Warming, Cock Worship, Collars, Come Inflation, Creampie, Crossdressing, Cuckolding, Cum Eating, Dacryphilia, Deepthroating, Degradation, Dirty Talk, Distended stomach, Dominance, Double Penetration, Dry Humping, Ecto-Genitalia (Undertale), Ecto-Penis (Undertale), Ecto-Tongue (Undertale), Ecto-Vagina (Undertale), Exhibitionism, Explicit Language, Explicit Sexual Content, Face-Fucking, Face-Sitting, Fear of Discovery, Feeding Kink, Fellcest - Freeform, Fontcest, Formalwear, Foursome, Frottage, Fucking Machines, Gender-neutral Reader, Glory Hole, Hand Jobs, Haphephobia, Hate Sex, Humiliation, Implied/Referenced Character Death, Implied/Referenced Self-Harm, Intercrural Sex, Kinktober 2018, Knotting, Lactation, Lapdance, Licking, Light Masochism, Light Sadism, Lingerie, Marking, Master/Pet, Master/Servant, Masturbation, Mating Cycles/In Heat, Medical Kink, Mirror Sex, Misuse of Bone Attacks, Multi, Multiple Orgasms, Muscles, Nipple Piercings, Nipple Play, Non-Consensual Bondage, Object Insertion, Omorashi, Oral Knotting, Oral Sex, Orgasm Delay/Denial, Outdoor Sex, Overstimulation, Pantyhose, Possessive Behavior, Praise Kink, Predator/Prey, Prostitution, Public Humiliation, Punishment, Rape/Non-con Elements, Roleplay, Rough Sex, Rutting, Scars, Scents & Smells, Seduction, Semi-Public Sex, Sensory Deprivation, Sex Toys, Shibari, Shotgunning, Shower Sex, Size Difference, Sleepy Sex, Sounding, Spanking, Spitroasting, Stripping, Suspension, Swapcest - Freeform, Temperature Play, Tentacles, Threesome, Tickling, Vaginal Fingering, Vaginal Fisting, Vibrators, Voyeurism, Wall Sex, distracted sex, eye socket sex, maid outfit, pillow humping, primal play, swapfellcest - Freeform
Language: English
Status: In-Progress
Published: 2018-10-01
Updated: 2019-05-16
Packaged: 2019-07-23 04:27:46
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 34
Words: 36,955
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16151600
Author URL: https://archiveofourown.org/users/Vexatious/pseuds/Vexatious
Summary: Tags/Pairings shown at the beginning of each chapter.





	1. Introduction: The Jerry Show

The author straightened her back, wiggling her fingers in preparation to begin typing her Kinktober series for the year. She laughed maniacally to herself. Her Kinktober would be Jerry-centric this year, a Kinktober to end all Kinktobers! The cursor on the open Google Document beckoned her, and she answered the call.

_ Jerry stepped through the door, high heels clicking on the tiled floor. Though he resembled a doughy, pock-marked sombrero in appearance, Jerry possessed the biggest, thickest- _

‘Excuse me,” Jerry interrupted the author indignantly, “did you just call me a doughy sombrero?”

“Mm-hmm,” she replied, distracted by the flood of 3AM writing inspiration. “Pock-marked too. Doughy, pock-marked sombrero. Or maybe a malformed but somehow endearing potato?”

Jerry gasped. “Hey, you’re no looker yourself, lumpy human. I came in here to tell you that your wi-fi is slow and your cable doesn’t include the Bravo network, not to be openly mocked.”

“I didn’t mock you openly. You snooped,” she pointed out.

Jerry ignored her, perusing the list of kinks available for each day of the event. “Good thing I did. These kinks are so vanilla. Ugh. I wouldn’t be caught dead participating in any of this.”

“Vanilla?” sputtered the author, confused. These all seemed like legitimate kinks to her. Ok, maybe there wasn’t an oviposition or SOUL sex option, but no way were distention and omorashi vanilla!

“Va. Nil. La.” repeated Jerry, pulling on a neon green crab fursuit. “Peace out. I’m going yiffing!”

The author immediately scrubbed all thoughts of Jerry and furry fuck parties from her mind and forced herself to forget about her original Kinktober plans and Jerry’s existence completely. I guess it’ll be skeletons then, she thought.

She resumed typing.


	2. Day One: HoneyBBQTacos (Deep-throating, Face-sitting, Cum Inflation)

**Summary for the Chapter:**

> Pairing: US!Papyrus x US!Sans x SF!Papyrus (HoneyBBQTacos, SweetPuppyBerry)
> 
> Featured Kinks: Deep-Throating, (Cum) Inflation, Face-sitting
> 
> Additional Warnings: Swapcest/fontcest, Threesome, Begging, Oral Knotting

Normally, Blue avoided his brother’s filthy and cluttered bedroom like the plague, preferring to pretend that such blatant and unaddressed squalor did not exist in his own home. He’d merely entered the room in an attempt to collect laundry, and when Stretch, his lazy brother, had suggested that Blue try face-sitting with him, he assumed the lanky skeleton was joking.

Minutes later, Blue found himself straddling his brother’s face, thighs squeezing the other skeleton’s skull, trying to maintain even a slight modicum of decency and failing. He rolled his hips, questing for more of his brother’s tongue. Stretch lapped and suckled at Blue, making sure to pay attention to his hotspots- his swollen clit and the sensitive spaces deep inside of him.

Blue threw back his head and screamed in ecstasy as his brother’s tongue curled and twisted in his tight little pussy.

“MWEH… PAPY… YES… YES… YE-MMMFFF!”

Stretch opened an eyesocket when his brother’s mewling voice trailing off into choking and gagging. He never stopped plunging his tongue into the plump pussy pressed into his face, but he could see the underside of a pierced, dark orange ectocock sliding in and out of Blue’s mouth through the blue magic of his brother’s thighs framing either side of his face.

Squeezing Blue’s firm, round ass, Stretch lifted him up slightly, freeing up his mouth momentarily.

“hey, Mutt, i said you could sleep on our couch not face fuck my brother,” he snapped, irritated at the appearance of an uninvited rival.

“yer bro was screamin’ too loud for me to sleep. thought i’d quiet ‘im down a bit,” growled Mutt, pulling out of Blue’s mouth briefly to reply.

“DON’T STOP,” Blue gasped, panting. “I’M SO CLOSE. FUCK ME. BOTH OF YOU. PLEASE FUCK ME!” Blue begged.

“you heard ‘im,” said Mutt with a smirk, cramming his cock back down Blue’s throat all the way to the knot at its base. Blue gulped around the massive shaft, sweeping his tongue along as much of the length as he could.

With an reluctant grumble of agreement, Stretch pulled his brother’s pussy back to his mouth. The hard thrusts from Mutt rocked Blue against Stretch’s face, so the prone skeleton grabbed hold of Blue’s thick thighs to steady him as he plunged his tongue back into the tight waiting warmth.

Stretch pumped with his tongue while Mutt pumped with his cock. Mutt’s thick shaft filled Blue’s mouth all the way down into his throat so far that Blue couldn’t even suck properly. He just braced himself as the cool metal of Mutt’s piercings dragged across his tongue and gagged on the too-large cock repeatedly hitting the back of his mouth and invading his summoned throat.

Blue clutched desperately at Mutt’s hip bones, holding onto the other skeleton’s bucking body as tension built in his own core. Drool leaked from the corners of his mouth; he bobbed his head to match Mutt’s rhythm, taking the knot at last, eyelights rolling back in his sockets at the impossibly deep penetration.

Suddenly, Blue’s pussy slammed down hard on his brother’s face. Stretch thanked his inability to actually smother as Blue’s hot cum gushed from his pussy and into his brother’s mouth. The hot throbbing cunt became Stretch’s whole world for a brief heavenly moment, the taste and scent assaulting his senses in the best possible way.

“fuck… fuck…” groaned Stretch. He heard Mutt growl and knew that the other skeleton was close. Blue had already orgasmed. No way was Stretch going to miss out on his own blissful release.

Quickly lifting his brother again, Stretch slid himself forward, lined up his cock, and hilted himself in Blue’s pussy just in time.

Blue could do nothing more than barely cling to his pleasure-hazed consciousness. Stretch came hard, shooting hot cum deep inside him where it glowed through his translucent ecto-flesh low in his stomach. Stretch held on tightly to Blue’s hips, pouring more and more thick ropes of orange magic into his brother.

With a final jerk of his pelvis, Mutt followed Stretch’s example, only his load spilled directly down Blue’s throat. No matter how much sticky cum the smaller skeleton gulped down, Mutt kept producing more, emptying his knot down Blue’s throat and into his stomach until it started to swell with the sheer volume of magic from both sources.

Dark orange cum overflowed Blue’s mouth as he tried in vain to keep swallowing. It dribbled down his chin and dripped down his front onto his brother’s stomach. All three skeletons collapsed in a heap on Stretch’s worn mattress. They were too exhausted and sex drunk to even bother cleaning themselves up.

Blue drifted to sleep with Mutt and his brother each resting a hand on his stomach which bulged with swirls of both light and dark orange magic.


	3. Day Two: Fellcest (Ass Worship, Begging, Medical Play)

**Summary for the Chapter:**

> Pairing: UF!Papyrus x UF!Sans (Fellcest)
> 
> Featured Kinks: Ass Worship, Begging, Medical Play
> 
> Additional Warnings: Fellcest/fontcest, Bondage, Sounding, Spanking, Biting, Anal Sex, Anal Fisting, Creampie

“i’m starting to suspect that you aren’t a real doctor,” quipped Red as he surveyed the new set-up in their basement sex dungeon. Boss had recently acquired a medical examination table, probably from that psychotic lizard nerd, Alphys. A tray of questionable instruments stood next to it, gleaming in the overhead light. “where’d you get your degree from again?”

“I GOT IT FROM S-T-F-U SANS, NOW TAKE OFF YOUR FUCKING CLOTHES AND GET YOUR FEET IN THE STIRRUPS,” snapped his brother, shoving him forward roughly. Grumbling about the lack of a gown, Red obeyed. He should have known better than to agree to this. Those tools probably weren’t even sterile.

“ON YOUR STOMACH, SANS,” ordered Edge.

“i don’t think that’s how these things work, Boss…” Red followed the instructions despite his complaint.

“I SEE YOUR FACE ALL DAY, SANS, AND I’M TIRED OF LOOKING AT IT. I WANT TO SEE THAT FAT, SEXY ASS OF YOURS. SUMMON IT. NOW.”

Red rarely made the effort to conjure his ectobody; he considered it a waste of magic and too much of a temptation for handsy barflies at Grillby’s. Only Boss knew how plump and round his ass looked, and the scarred skeleton wasn’t interested in sharing. Red’s bright cherry red magic formed around his lumbar region, pelvis, and femurs. Boss made a low and appreciative growl, running one sharpened phalange down his brother’s spine, and making the smaller skeleton shiver in anticipation.

“A PRECAUTION,” said Edge, fastening padded cuffs around Red’s ankles and wrists and attaching them to the examination table. “ANOTHER PRECAUTION.” With those words, Edge reached under Red’s stomach and cupped his thick cock. He rubbed the beads of precum that leaked from the tip of Red’s shaft with his thumb. Having located his brother’s urethra, Edge quickly inserted a vibrating urethral sound into the hole.

“hey! what’s that for,” protested Red.

“I DON’T WANT YOU TO CUM AND THEN FALL ASLEEP LIKE YOU DID LAST TIME WE TRIED A NEW GAME,” growled Boss, circling the captive skeleton like a sleek predator. Red looked good enough to eat, and Boss was starving.

Standing behind Red once more, Boss dug his fingertips into Red’s sides and dragged them back until his hands were resting on the steep rise of Red’s ass. Edge kneaded the supple flesh like a contented cat before giving one cheek an experimental slap to watch it jiggle then darken in the shape of his handprint.

“I CAN’T BELIEVE SUCH A DELECTABLE MORSEL BELONGS TO A DISGUSTING MONSTER LIKE YOU,” Edge mused.

“just blessed, i guess,” grumbled Red, trying to ignore the stimulation in his cock that both made him want to cum and prevented him from doing so.

“WE’LL SEE IF YOU STILL CONSIDER YOURSELF BLESSED WHEN I’M THROUGH WITH YOU,” Edge stated ominously. Leaning down, he bit one of Red’s chubby ass cheeks, licking at the blood that welled from the mark.

The taste of blood only whetted Edge’s appetite for the main course, but like any connoisseur of the finer things in life, he dragged out the experience, savoring every moment. With a bestial growl, Edge pounced, grabbing Red’s ass, one hand on each cheek, gripping the ectoflesh so tightly that the tips of his phalanges sank in and the tender flesh puffed up in the spaces between his fingers.

Red groaned in pleasure at the sensation of Edge’s palms kneading his ass, pulling at it, releasing it, and occasionally delivering a hearty slap. Edge’s breathing became ragged. He couldn’t resist the temptation any longer. Spreading Red’s ass, Edge gazed with hungry anticipation at Red’s tight, unprepared asshole, just waiting to be sampled… and then completely destroyed.

Slick with dark red magical saliva, Edge’s long tongue probed and explored the puckered entrance, slowly forcing its way inside, only to withdraw and plunge in further. Red rocked his hips in vain, dragging his throbbing, engorged cock along the padded surface of the exam table. Nothing relieved the building pressure low in his abdomen.

Sharpened teeth scraped Red’s ass cheeks. Edge buried his face between the ample mounds, twisting and curling his tongue inside of his mewling, writhing brother. Edge’s belt buckle clattered to the floor as Edge unfastened his pants, releasing Red’s ass with one hand to palm his thick, spiked erection. Time for dessert.

Red knew what was coming when his brother pulled away from him to line up his cock with his still too-tight asshole. He hurried to protest, but his pleas, as usual, did nothing to deter Edge from his own satisfaction.

“wait, Boss, that’s not enough foreplay for-”

“IT’S ENOUGH FOREPLAY FOR ME,” snapped Edge, forcing the head of his cock inside of his brother. He gave the smaller skeleton’s ectoflesh only a few seconds to stretch around him before he bucked his hips, slamming the rest of his length into Red’s ass. Red screamed, agony mixed with ecstasy. He felt so full that he might break, and he loved it.

Edge pounded into Red with reckless abandon- hard, fast, and utterly merciless. His sockets closed as he lost himself in waves of pleasure. If only Red would stop ruining the moment with his incessant shrieking.

“take it out, Boss. please, take it out. please, Boss let me cum!” Red babbled over and over, struggling against the padded manacles in an attempt to paw at the vibrating urethral sound blocking him from orgasm.

“SHUT UP, SANS, OR I’LL REALLY GIVE YOU SOMETHING TO SCREAM ABOUT.” Edge pulled Red’s hips backwards against him each time he thrusted forward. His cock sank in so deep, and Red’s tight asshole squeezed him so exquisitely. Edge had more activities planned than just rough anal sex though, and if he waited much longer, he’d finish inside Red and sabotage his own fun.

Red whimpered and mewled. “please,” he cried, delirious with over-stimulation and his inability to cum. “please, Boss, please.”

“I WARNED YOU, SANS.” Edge pulled out, exerting every ounce of self-control to keep from cumming then and there and spilling his hot load all over Red’s round ass while his brother begged him for mercy.

The tall skeleton perused the selection of medical devices gathered on the nearby tray table. His elegant gloved hand passed over a scalpel and a dangerous-looking spiked Wartenberg wheel in favor of a large hand-crank speculum. Red would regret his incessant racket soon enough.

Edge didn’t bother lubricating the speculum; he simply shoved it into Red’s waiting asshole and began to turn the crank, spreading Red wide open with ease. Red enjoyed the sensation well enough at first, but Edge just kept going, right on past Red’s comfort zone.

“yer cock ain’t that big!” complained Red, momentarily forgetting about the urethral sound as the delicious fullness in his asshole became too much to handle.

“IT’S NOT MY COCK YOU HAVE TO WORRY ABOUT,” replied Edge cryptically.

“yer gonna tear my ass open!”

“THAT’S THE PLAN.”

“wha-”

Edge slammed his fist into Red’s ass almost up to the wrist, cutting off his brother’s words. The speculum blades scraped the skeleton monster’s carpals though his gloves, but Edge didn’t stop. Inch by excruciating inch, he pushed his hand in deeper. Fuck, Red was so tight, and splitting him open felt so good. Edge pumped his cock with one hand while the other slowly disappeared inside of his brother.

Red’s eyelights rolled back, and his tongue slid out over his pointed teeth. Panting and drooling, Red moaned and babbled gibberish. Edge started thrusting viciously with his hand, pulling slightly backwards only to plunge deeper into his brother’s ass until he was elbow deep in the clenching warmth.

Increasing his already punishing pace both jacking off and fisting his brother’s ass, Edge hurtled towards climax. Maybe he would relent and allow Red to enjoy the experience too. Edge let go of his cock, withdrawing his arm almost completely from Red’s abused hole. He yanked the vibrating sounding rod from his brother’s swollen, throbbing cock just as he forced his arm back inside of him- past, the elbow this time.

Red came hard, splashing the table with sticky globs of cherry red cum. Edge removed his arm from Red once more, lining up the head of his cock with Red’s gaping hole just in time to spill his hot load in Red’s quivering asshole. The speculum held Red wide open for Edge to survey his conquest.

“I’M GOING TO GO SHOWER,” Edge announced after taking in the glorious sight of Red’s round ass, cheeks spread, cum dribbling out of his utterly destroyed asshole for several long minutes. The tall skeleton turned to leave, chased by Red’s querulous voice.

“wait… Boss, you forgot to untie me,” he shouted, his position on the examination table preventing him from seeing anything other than a limited space in front of him.

“UNFORTUNATELY, THEY DIDN’T OFFER BEDSIDE MANNER AS PART OF THE CURRICULUM AT MY ALMA MATER.”

“you don’t have an alma mater! Boss?  _Boss!_ ”


	4. Day Three: Grillster (Sensory Deprivation, Temperature Play)

**Summary for the Chapter:**

> Pairing: Grillby x W. D. Gaster (Grillster)
> 
> Featured Kinks: Sensory Deprivation, Temperature Play
> 
> Additional Warnings: Bondage

Gaster collapsed onto the stool at his friend Grillby’s bar and restaurant, exhausted after another marathon of sleepless nights working on his top secret SOUL research as the King’s Royal Scientist. On the surface, the job seemed like a dream come true for the intelligent and motivated doctor, but the dream has turned into a nightmare of failed experiments and devastating setbacks.

He needed a stiff drink. In fact, he needed about ten stiff drinks, and he was already halfway there and extremely tipsy when Grillby cut him off for the evening.

“I’m fine,” Gaster slurred when Grillby refused to refill his tumbler with more fire whiskey.

“You’re drunk,” corrected Grillby gently, “and you already looked haggard and overworked when you came in. I don’t think alcohol is going to help you.”

Gaster snorted mulishly, but he didn’t disagree. He trusted Grillby, and he knew the bartender only had his best interests at heart with the scolding.

“I just don’t know how much longer I can deal with the stress of my research,” the weary Royal Scientist admitted.

“How about I close early tonight, and we can go upstairs to my apartment and blow off some steam,” offered Grillby.

Gaster couldn’t refuse. Nothing relaxed him quite like a bedroom session with Grillby. In addition to making a five-star burger and fries, the fire elemental was a master of sensory deprivation and temperature play. Giving up control to someone else sounded perfect to a monster currently overburdened with responsibility.

Once the last patron swallowed their last bite of food, washed down by the last dregs of their drinks, Grillby flipped his business sign from OPEN to CLOSED.Gaster abandoned his sobering glass of water and sleeve of crackers to follow his friend upstairs. His head already partially cleared, Gaster now looked forward to some casual and kinky fun.

Instead of turning on the lights, Grillby lit his own way to the bedroom, leaving Gaster to stand in the darkened entrance to his apartment, awaiting his return. Grillby called out from the bedroom, instructing Gaster to strip down and leave his clothing in the entryway, and the Gaster complied without question.

The fire elemental emerged from the bedroom with a box of sensory deprivation and bondage equipment. He blindfolded and gagged the slender skeleton and placed noise blocking headphones over his skull before leading him by the hand to his living room. Grillby pushed the sofa and coffee table out of the way and guided Gaster into a kneeling position on the floor.

A spreader affixed to Gaster’s lower legs held him in locked in the position, and Grillby gently pulled his friend’s arms behind his back and tied his wrists together, attaching the skeleton monster’s bound hands to the spreader with an expert knot. Grillby’s hands itched to do some shibari knotting with Gaster at his mercy, but the tense night called for tenderness rather than the intricacies of silk rope bondage. Grillby stepped away from Gaster, allowing the suspense to build as the scientist wondered where Grillby would touch him and when.

The fire elemental lowered his flames, cooling his temperature to a pleasant warmth. Circling Gaster, he leaned forward and slid one hand up the other monster’s neck. A gust of warm moist breath tickled the skeleton’s jaw. Grillby was close enough to kiss him, holding his head in place with a firm hand on his throat, but he withdrew, leaving Gaster moaning weakly into his gag.

Grillby let several minutes tick by before he touched Gaster again. This time he increased the heat in his fingertips so that his touch would be intense but not painful. Crouching behind the skeleton, Grillby trailed his flaming fingers down Gaster’s spine, leaving the scent of warm bone hanging in the air.

The fire elemental’s warm orange glow met with competition as a glowing purple cock slowly coalesced on Gaster’s pelvis. The complementary colors cast dancing shadows across the two monsters captured in their radiance, the beauty completely lost on the blindfolded skeleton.

Removing his hands from his friend’s body, Grillby shifted himself to face Gaster, taking in the pulsing, erect length in front of him. It was still too early to let the night descend into passionate sex, but that didn’t mean Grillby couldn’t pause to appreciate the cock that the skeleton monster had summoned.

Opening his mouth wide, Grillby moved his mouth to cover the pulsating cock whose heat nearly matched his own. Gaster felt the ghostly sensation of Grillby’s mouth not quite touching him, and his cock twitched, freeing a bead of precum which dripped onto Grillby’s tongue, sizzling away to nothing in the flames.

Grillby backed away, letting Gaster’s dick bob in the cooler air that now caressed it in his absence. The fire elemental had to calm his own breathing, reminding himself not to rush. The whole point of this session was helplessness and giving up control. Libido could wait until later, though Grillby’s magic ached to form into a cock of his own.

In order to calm the fiery lust uncurling in his loins, Grillby paced. When the insistent need in his core cooled, he returned to Gaster, licking his sternum with flames that ranged from lukewarm to bordering on the unbearable. The skeleton arched his spine into the stimulation, and once more, Grillby backed away. The longer the sensory deprivation lasted, the more satisfying it would be.

The fire elemental monitored his friend closely, watching beads of sweat form on Gaster’s skull and slide down the smooth bone in ever-changing paths. Gaster’s erection subsided, the magic of his cock beginning to dissipate. Thoughts of the many tasks that awaited him tomorrow at the Laboratory crowded his mind. Grillby watched the tension- tension of a different kind- regain its hold upon his friend.

Each time his friend’s anxiety resurged, Grillby redirected his attention to some other part of his body. Grillby’s tantalizing touches both seared and soothed the skeleton scientist. Warm, crackling hands stroked Gaster’s spine, fingertips finding the spaces between the vertebrae. The magic of Gaster’s cock hardened again, engorged and throbbing from the teasing touches.

Grillby repeated the ritual again and again. Each time he aroused Gaster until the skeleton gasped and moaned into the gag, then he removed all contact and made the other monster wait. During sensory deprivation sessions, time played strange games. A single second could easily occupy an hour; an hour could pass in the blink of an eye. As time both crawled and sped by, Gaster’s reactions to the stop-and-go stimulus changed.

At first, the skeleton monster’s mind spun with thoughts of responsibilities and failures in the silence and darkness of his confines whenever Grillby stop touching him or teasing him with ever-changing temperature levels. Grillby watched his friend visibly slump each time the fatigue of the burdens of his job weighed him down once more.

Gradually, as the session progressed, a quivering anticipation replaced the defeated wilting. Gaster couldn’t focus on stress if he was seeking the heated pleasure of Grillby’s exploring hands and mouth. The inner reflections on his problems melted away into a very obvious, lust-charged wait for more of Grillby’s attention. The real world and its problems faded away under the nearly orgasmic intensity of anticipating the next sensation.

A satisfied smile spread across the dancing flames of Grillby’s features. Gaster’s surrender deserved a reward, and though the headphones blocked out the sound of Grillby unfastening his pants, the skeleton would find out soon enough what the next source of contact would be. They had both waited long enough; it was time to release the last of their stress.

Grillby left the bindings on, and it enhanced the sex exponentially. Just as the bartender intended, his skeleton friend sank into an exhausted but restorative slumber mere moments after cumming. Tomorrow would be another beleaguered day, but for tonight, the Royal Scientist rested peacefully in the fire elemental’s perfectly warm arms.


	5. Day Four: SpicyKustard (Spanking, Mirror Sex, Spit-Roasting, Dacryphilia)

**Summary for the Chapter:**

> Pairing: UF!Papyrus x UT!Sans x UF!Sans (SpicyKustard, Kedgeup & Mustard)
> 
> Featured Kinks: Spanking, Mirror Sex, Spit-Roasting, Dacryphilia (Crying)
> 
> Additional Warnings: Gaping, Socket Fucking, Heat Cycle, Threesome

Sans’ heat cycle hit so quickly and intensely that he had little choice but to show up at his neighbors’ doorstep, begging to be fucked senseless with tears already gathering in the corners of his sockets.  Now those tears streamed freely down his cheeks as two thick red cocks slammed into him- one at his mouth and one in his needy pussy.

Edge held Sans bent forward, and Red fucked his throat roughly, knowing that the only way to relieve his lover’s relentless heat was to destroy him from both ends. Red’s phalanges scraped his boyfriend’s skull, bracing himself as he came for the… third? fourth?.. time. Edge grunted as he followed suit. The Fell skeleton brothers’ magic poured into Sans’ pussy and throat, but they didn’t stop.

With no warning or preparation, Edge pulled out of Sans’ pussy and plunged his cock to the hilt into the whimpering skeleton’s asshole. The new, tight hole made Edge close his sockets and tilt his head back in pleasure. Red watched his brother pound his boyfriend’s asshole, nearly turning it inside out with his ferocious pace. The mirrors that they had set up in the bedroom showed Sans’ gaping pussy with Edge’s crimson cum oozing out of it, bubbling out steadily with each rough thrust.

“fuck, that’s hot,” chuckled Red. Sans pawed at Red’s cock, recapturing his boyfriend’s attention. Red gazed down at Sans’ crying face, cum dribbling from the corners of Sans’ slack mouth spurring him on to pry it open with a thumb for another round. Sans had other ideas though.

“my socket, fuck my eye socket,” the heat drunk skeleton begged desperately, guiding Red’s cock up to his darkened right socket.

“anything for you, babe,” Red murmured, tearing his attention away from the plump and swollen pussy visible in the mirror to focus on his boyfriend’s request. His cock caught on the rim of Sans’ eyehole, making him gasp, but the tears lubricated the socket enough for Red to start fucking it in earnest.

A hearty slap punctuated each thrust of Red’s throbbing shaft into Sans’ skull. Edge spanked Sans’ round ectoflesh, making the supple magic of his ass jiggle and clench around the massive girth penetrating it. Red watched the purple handprints form against the blue of his boyfriend’s magic in the mirror, and Sans moaned with each noisy contact.

Edge grew impatient with Red’s gentle pace, so he increased the force of his bucking hips, slamming Sans forward and impaling his socket on Red’s cock over and over again.The smooth interior bones of Sans’ skull stroked Red’s cock just right, and it wasn’t long before he was close to yet another orgasm.

Rising onto his tiptoes to maximize the depth of his fucking, Edge groaned. His movements hitched, and he came, filling Sans’ asshole to overflowing. The sight of the crimson cum welling around his brother’s cock and spilling out of Sans’ asshole to join the cum dripping from his pussy pushed Red over the edge.

Sans gripped Red’s hipbones tight, and Red grasped the sides of his boyfriend’s skull as his cock twitched and pulsed, shooting hot seed straight into his boyfriend’s skull. When he finally withdrew, cherry red cum mingled with the tears overflowing Sans’ sockets. Sans had never looked so thoroughly satisfied or so gorgeous as he smiled up at Red.

Red knelt down and licked the mixture of tears and cum from his exhausted boyfriend’s face. He captured Sans’ mouth in a deep and hungry kiss. Nothing tasted better to Red than his cum on his boyfriend’s tongue.


	6. Day Five: Fell Sansby (Sadism/Masochism, Feederism, Shotgunning)

**Summary for the Chapter:**

> Pairing: UF!Grillby x UF!Sans (Fell Sansby)
> 
> Featured Kinks: Sadism/Masochism, Feederism, Shotgunning
> 
> Additional Warnings: Choking, Burning/Branding

Fellby watched Red eat with an almost obsessive attention. Sharp teeth, one gleaming gold, tore through bread and into medium rare burger meat, the juice and mustard dribbling down his chin. The extravagantly dressed purple fire elemental wanted nothing more than to bend the stout skeleton over a table, shove his face into a plate of fries, and fuck his asshole raw.

Why else would the bar owner let Red spend so much time stuffing his face without demanding that he pay his extensive tab? Fellby actually prepared every single one of Red’s meals himself just for the perverse pleasure of watching him eat. Today, though, that particular pleasure wasn’t enough.

It was time to collect a debt.

“Red, come into my office,” ordered Fellby once Sans finished swallowing his final mouthful of mustard-soaked fries. “We need to discuss your lengthy tab.”

Red wiped the corner of his mouth on one of his sleeves, smearing the fabric with Fellby’s signature homemade mustard. “aww, c’mon, you know i’m good for it,” the stocky skeleton protested, though he dutifully followed the fire elemental into the aforementioned office, making no comment when Fellby closed and locked the door behind them.

Red fished a cigar out of his pocket, planning to indulge in some after-dinner smoking.

“I think,” Fellby purred dangerously, plucking the cigar from Red’s hand, “that I may require a down payment.” Fellby closed his hand over the cigar, incinerating it instantly with his violet flames. Leaning close to Red, the fire elemental opened his mouth and let a gust of fragrant cigar smoke drift free.

Closing his sockets, Red inhaled. If he couldn’t smoke the cigar himself, at least he could enjoy the scent and flavor secondhand. Red followed his nasal aperture forward until his and Fellby’s faces were nearly touching. “mmm,” he hummed. “i think i prefer it this way. kinky, huh?”

“You have no idea,” chuckled Fellby darkly. Without warning, the fire elemental grabbed the skeleton monster by his jacket and tossed his backwards onto his mahogany office desk, scattering unimportant papers and writing utensils to the floor. Red sputtered in shock but didn’t fight back when Fellby used his jacket to pin his arms behind his back, nor did he make any attempt to stop Fellby from ripping away his basketball shorts. His cherry red cock gave away his eagerness to see what would happen next.

Fellby let his crisply pressed trousers fall to the floor, letting loose his own glowing erection. Red smirked, probably in preparation for a joke or pun at Fellby’s expense, but the bartender cut him off by pressing a hand firmly to Red’s throat and squeezing. Skeletons couldn’t suffocate, but the sensation of choking was still unnerving and exhilarating to Red. Fellby relaxed his hold, allowing him to sputter for air for only a brief second before tightening his grip again.

Fellby’s other hand deftly spread Red’s ample asscheeks, and two pleasantly warm fingers slipped inside of his asshole. Fellby fingered Red’s ass roughly, scissoring his fingers inside of the constricting entrance, though he skimped on foreplay and removed his fingers after only minutes of stimulating and stretching Red’s hole. It would have to be enough because the tip of Fellby’s cock already rubbed at the poorly prepared entrance.

When Fellby released Red’s throat a second time, the skeleton managed to gasp out just a single word “more!” before the flexible bones of his neck were crushed again in Fellby harsh grip.  _So the cocky shit wanted more, did he?_

The fire elemental splayed his hand over Red’s sternum and increased the intensity of his flames, reducing Red’s sweater to ash and scorching his bones with the curling flames. Red’s back arched, though Fellby’s hand around his neck held his head to the wooden desk top. A red magical tongue, coated in saliva, flopped out of the corner of Red’s mouth, strings of the spittle dripping down onto the expensive wood of Fellby’s desk.  _Disgusting._  Fellby loved it.

Inch by inch, to the sound of his lustful staccato growls, the fire elemental’s fiercely bucking hips forced his thick cock into Red’s asshole. The narrow opening squeezed him deliciously, and when he began to slam in and out, his cock caught on the rim of Red’s ass. The dragging sensation along the underside of his shaft felt amazing, and he couldn’t get enough.

Each time Fellby’s hips snapped forward, he seared the sensitive underside of one of Red’s ribs with a white-hot finger. The fire monster alternated between choking Red until he gurgled and drooled and allowing him to breath freely and scream with the mixture of pain and pleasure from the blistering trail of Fellby’s touches. 

Every now and then, Red regained just enough of his senses to plead for “more,” “hotter,” or “faster,” and Fellby delivered, igniting pleasure that coursed through the masochistic skeleton’s bones like wildfire.

* * *

Fellby tossed Red a hand towel to clean himself up; the fire elemental’s flames had already burned away all traces of their tryst on his fiery flesh. The pair straightened their clothing before returning to the restaurant, and Red zipped up his jacket to cover his bare, burned ribs and bruised vertebrae.

Fellby strode confidently back to his place behind the counter, features arranged in an expression of smug victory, and Red dragged himself up onto one of the barstools, hissing as his tender ass connected with the padded seat.

“Really, Red?” asked Fellby, raising a dapper brow at the cheeky skeleton.

“c’mon, Fellbs, i’m famished. i need to recharge,” wheedled Red.

“Fine,” Fellby conceded, “but it’s going on your tab.”


	7. Day Six: Swap Papgore (Cock Worship, Biting)

**Summary for the Chapter:**

> Pairing: US!Papyrus x US!Asgore (Swap Papgore)
> 
> Featured Kinks: Cock Worship, Biting
> 
> Additional Warnings: Size Difference, Knotting

Stretch never imagined that his knock-knock joke marathons at the door to the Ruins would lead to this. When he first saw his fellow jokester’s ruggedly handsome face, he’d hoped though.

Now Stretch found himself kneeling in front of the former King with a glossy pink cock resting against his cheekbone. Asgore’s erection was befittingly enormous, displaying a prominent knot as it slid free of its furry sheathe. Resting his hands on the soft, white fur of the goat monster’s thighs, Stretch nuzzled the warm, sticky surface as desire stirred his own magic.

“Ah, my friend, it has been years since I received such attention,” murmured Asgore, stroking Stretch’s skull as the skeleton monster’s smooth, cool bones coaxed a bead of precum from his twitching length. Stretch summoned a tongue to lick up the offering.

Instead of responding to the King’s words, Stretch let his tongue continue to travel from the tip of Asgore’s mighty cock to the base. The skeleton monster placed kisses all over the bulging knot, humming his pleasure as the huge shaft bobbed against his face. Stretch then used his tongue to stroke the throbbing underside of the goat monster’s cock back up to the head. The taste was intoxicating.

Asgore stayed still, sitting relaxed in his comfortable chair while Stretch worshipped his cock with his mouth and tongue. The skeleton monster licked, kissed, and gently nipped along the entire substantial length of his cock, and when that wasn’t enough, he used one of his hands to slowly stroke up and down the former King’s length as well.

Closing his sockets, Stretch opened his mouth wide to encompass the tip of Asgore’s cock; the head alone was quite a mouthful. Stretch flattened his tongue, guiding the leading inch of it further into his mouth, and began to suck, moving his head up and down in time with his hand. Asgore groaned in pleasure, trying to keep from bucking his hips and fucking Stretch’s throat raw.

Every time Stretch rocked forward, he took a little bit more of the former monarch’s length until the King’s cock finally penetrated his throat. He gagged, but didn’t stop sucking and bobbing his head, mewling hungrily as he worked himself into a sexual frenzy. He couldn’t get enough of Asgore’s huge cock. He wanted more, more, more!

Gasping, Stretch released Asgore’s cock from his mouth, strands of saliva and precum slowly stretching out between them before breaking apart. “your majesty, please, i… i need your cock,” Stretch whimpered, turning around and bending over to present his dribbling pussy entrance to the goat monster.

“You do not need to call me ‘Your Majesty.’ I much prefer my given name,” replied Asgore mildly, “which I’m sure you’ll be moaning quite lewdly in a moment.” The former King lifted his friend delicately by the femurs, still facing away from him, and positioned the skeleton’s fluttering entrance over his waiting erection. “Please let me know if I’m hurting you.”

With those words, Asgore began to lower Stretch onto his cock. It was a painfully slow entry. The King’s girth split Stretch open so wide that the skeleton could do no more than ride out the waves of bliss as the King pushed into him, stretching and filling him further than he ever thought possible. His magic could barely contain the goat monster’s formidable member.

Stretch’s slick arousal soon coated Asgore’s cock, dribbling down onto the knot at the base. Gravity and the powerful upward thrusts of the King’s broad hips finally managed to seat Stretch fully on the oversized shaft. Stretch’s eyelights rolled back in his sockets. The massive length inside of him spread him almost unbearably wide; Asgore’s cock barely fit into his pelvic inlet. The pressure on his pelvic symphysis made him gasp and shiver at the teetering precipice of orgasm.

“I am going to move now,” announced Asgore.

“yes,” mewled Stretch desperately. He needed it. He needed Asgore to tear him apart with his magnificent cock and fill him to bursting with that glorious knot. “fuck me… fill me up!”

Stretch’s near-delirious pleas awoke the carnal beast in the soft-spoken former King. Bracing Stretch’s hips with his huge hands, Asgore slammed upwards into the skeleton so hard that his cock slid up into Stretch’s ribcage.  Asgore set a brutal pace, and Stretch flopped, limp and helpless, in the former King’s arms as his entire body was emptied and filled over and over.

Roaring along with his release, Asgore leaned down and sank his canines into the skeleton’s shoulder blade. His sharp teeth dug into the bone, leaving deep gouges. Stretch screamed, cumming at the same time as Asgore. Cum flooded his clenching pussy , so much that his magic couldn’t hold it. Asgore’s hot load burst through Stretch’s magic, soaking his ribs and pelvis.

Through the entire shared orgasm, Asgore held Stretch’s shoulder in his jaws. When the skeleton monster began to pitch forward, Asgore wrapped his arms around him to hold him up, kneading with with his hands and feet as his pulsing cock emptied his knot in and on his friend.

When Asgore was finally spent, he laid Stretch down on the sofa and brought him a blanket and some tea. “knock, knock,” murmured Stretch over his steaming mug of tea.

“Who is there?” asked Asgore reflexively.

“can weed,” replied Stretch with a sly but tired smile.

“Can weed who?”

“ _can we d_ o this again sometime?”


	8. Day Seven: Swapcest (Praise Kink, Aphrodisiacs, Incest)

**Summary for the Chapter:**

> Pairing: US!Papyrus x US!Sans (Swapcest)
> 
> Featured Kinks: Praise Kink, Aphrodisiacs, Incest
> 
> Additional Warnings: Fontcest/Swapcest, Begging

“PAPY, I BROUGHT YOU SOME OF YOUR FAVORITE HONEY!” Blue greeted his brother as the lanky skeleton slouched through the door to their home in Snowdin.

“what a coincidence, bro, because i picked you up one of those pastries you love from Muffet’s,” replied Stretch.

The two skeleton monsters exchanged their gifts, each watching the other like a hawk with too-wide smiles on their faces. Their eyelights stayed locked even as each of them lifted the proffered snack to their mouths.

Stretch guzzled the honey.

Blue munched the pastry.

Neither of them realized that his brother had spiked his present with potent drugs.

Later that evening the skeleton brothers sat on their couch together. Both of their bodies were stiff with tension, waiting for the aphrodisiacs they’d slipped into each other’s food to take effect. Blue fidgeted, watching Stretch out of the corner of his socket. Had it suddenly gotten warm in the living room?

Stretch tugged at the collar of his orange hoodie. He should’ve been watching Blue for signs of the aphrodisiacs taking effect, but cold droplets of sweat running down his neck distracted him. Would Blue notice him sweating? Would he suspect that his own brother had slipped drugs into his pastry? The feverish heat in his bones became unbearable, and he pulled off his hoodie, casting it aside and sitting on the couch in just a black tank top and khaki cargo shorts.

Blue squeezed his legs together, sure that Papy would notice the arousal soaking through his underwear and into his pants. His t-shirt felt like it was sticking to his bones from the sweat and heat pouring off of him. Why did Papy have to take off his hoodie. The sight of his brother in the clingy tank top made Blue’s mouth water. Surely the drugs would be kicking in soon?

“Don’t you think it’s a bit hot in here?” Stretch and Blue blurted out in unison.

The two skeletons laughed nervously into the silence that followed their identical statements. Stretch glanced at Blue; Blue glanced at Stretch.

Blue lunged forward at the same time that his brother reached for him. Their teeth clacked together, and their mouths opened and were quickly filled with each other’s tongues. The two skeletons swallowed each other’s mewls and moans as they hungrily pawed at their clothing. Stretch broke the kiss to remove his tank top, and Blue fumbled with his own shirt and pants in his hurry to get them off.

Breathing heavily, cock already in hand, Stretch watched Blue peel his soaked panties away from his arousal slicked pussy lips. Blue barely got them past his knees before Stretch’s mouth found his dripping slit nestled between his sensitive folds. Blue’s eyelights rolled back in his skull as his brother’s tongue teased his tight little hole.

“PAPY,” Blue wailed, arching his back as pleasure wracked his body.

Stretch moved away, licking up the juices around his mouth. His phalanges replaced his tongue so quickly that Blue didn’t have time to miss it. Even with the aphrodisiacs working in full force, Stretch paused to admire Blue’s exposed body, eyes sweeping over the elegant curve of each smooth, ivory bone.

Stretch whispered words of praise to his brother even as his fingers pumped in and out of him, the rapid movement and plentiful slick making wet slapping sounds.

“fuck, bro, you’re so… so gorgeous,” panted Stretch, unable to hold back the impulsive rocking of his hips as he fingered his brother. “everything about you is so perfect, so beautiful… your clavicles, your spine, your rib cage. i want to devour you. i want to make every part of you mine.”

“AH… PAPY… I’M SO… S-SO CLOSE.” Blue suddenly went rigid, and his tight cunt clamped down on Stretch’s fingers. Blue cried out as he squirted, coating Stretch’s hand in a gush of fluids. The orgasm did nothing to diminish Blue’s white-hot need though. He gasped and whimpered when his brother’s fingers stilled, and he wiggled his hips, seeking more of the toe-curling pleasure of his brother’s touch.

Stretch removed his fingers from his brother’s pussy and stuck them in his mouth, lining up his cock with Blue’s greedy, pulsating entrance. He ached to be inside of his brother, to fill Blue’s small body with his hot, sticky magic and watch it slowly flow back out of him when he couldn’t hold any more of it.

Rubbing his thick cock against Blue’s swollen, tender clit, Stretch continued his praises. “you’re so wet… mmm… feels so good.” His cock slid into his brother’s pussy with no resistance, and Blue’s sensitive walls clenched around it immediately. “oh fuck, you’re so… so tight…” Stretch propped the smaller skeleton’s legs up on his shoulders and began to thrust powerfully.

“MWEH… PAPY… TELL ME I’M A GOOD BOY,” whimpered Blue as the force of his brother pounding into him shook his small frame. Blue already felt another orgasm building as his brother filled him up over and over.

“you’re such a good boy, bro. so good. you’re squeezing me so tightly… good boy… good boy.. i’m gonna… gonna cum… be a good boy… and cum with me.” Stretch hilted in his brother again, and they came together, each of them screaming his brother’s name in the throes of ecstasy.

Aphrodisiacs still coursed through both of the skeleton brothers’ magic; they weren’t finished yet, not even close. Stretch fucked Blue for hours- on the couch, on the floor, against the wall. Finally, exhausted and riding out the waves of their final orgasms in the wee hours of the morning, Blue and Stretch curled up together on the couch for some much needed rest.

Blue closed his sockets with a satisfied sigh, nestled against his brother’s chest. Stretch drifted into slumber, stroking his brother’s skull absent-mindedly. Plots of future druggings played out in both of their minds, and smiles spread across their sleeping faces as they imagined all of the tantalizing possibilities.


	9. Day Eight: Kedgeup (Blood/Gore, Prostitution/Sex Work, Fisting, Hate Fucking/Angry Sex)

**Summary for the Chapter:**

> Pairing: UT!Sans x UF!Papyrus (Kedgeup)
> 
> Featured Kinks: Blood/Gore, Prostitution/Sex Work, Fisting, Hate Fucking/Angry Sex
> 
> Additional Warnings: CONTAINS NON-CON, character death mention

“hey, i’m sorry that your brother dusted and all, but i don’t think paying me to wear his clothes while you fuck me is going to help.” Sans’ matter-of-fact statement fell on deaf proverbial ears.

“I DIDN’T HIRE YOU AS A THERAPIST. I’M PAYING YOU TO SPREAD YOUR LEGS AND TAKE MY COCK LIKE THE PATHETIC WHORE YOU ARE.”

Sans didn’t mind the rough doggy-style sex; the scarred, edgy copy of his brother was a paying customer after all. He didn’t even mind the collar and leash. In fact, he kind of enjoyed the pressure against his throat while Edgy Mc Edgelord pounded away at his pussy from behind. Even the outfit, though strange, didn’t bother him, but the insults? Those were really killing any chance of Sans enjoying the experience.

“YOU LOVE MY COCK DON’T YOU, YOU CHEAP FUCKING SLUT,” Edge growled.

“hardly cheap,” muttered Sans under his breath. 

“DID I GIVE YOU PERMISSION TO SPEAK, YOU WORTHLESS PIECE OF SHIT?” snapped the taller skeleton, yanking hard on the leash and slamming his hips against Sans’ ass hard enough to leave a bruise on ecto-flesh already criss-crossed with deep, bleeding claw marks.

Sans sighed, biting back another snarky comment. _We need the money_ , he told himself over and over. Edge was paying handsomely for this session, and Sans couldn’t turn down that kind of cash.

Life on the Surface cost an arm and a leg, or in his case a pussy and a mouth, and if he wanted to provide his brother with all of the luxuries that they had missed out on as babybones in the Underground, he had to take any work he could get. Prostitution paid well and required minimal effort… most of the time.

“sorry, Boss.” Sans addressed the gruff skeleton as Boss as per his very specific instructions. 

“YOU AREN’T NOW, BUT YOU WILL BE, BROTHER.”

With a vicious SNAP, the burgundy leather end of the leash slapped Sans directly on his swollen clit, making him screech. His pussy clamped down around Edge’s cock, and the edgy skeleton’s cock ring dragged painfully against his sensitive walls. The sadistic skeleton continued to lash Sans’ clit without even slowing his thrusts.

Sans writhed, trying desperately to deflect the strikes onto a less tender part of his anatomy, but he couldn’t escape. Worse, his traitorous body responded to the new and unusual sensation of abuse. “wait, stop,” he whimpered, but the intense pleasure of an orgasm interrupted the flow of his words.

Edge ignored his protests; if anything, the smaller skeleton’s cries of pain only spurred him on to a more furious pace. He chuckled darkly when Sans’ pussy clenched and spasmed around his cock. “DON’T LIE TO ME, BROTHER. I CAN FEEL YOUR GREEDY CUNT BEGGING FOR MORE. YOU ALWAYS DID LIKE IT ROUGH, DIDN’T YOU?”

Sans shuddered as Edge hilted in him, digging his phalanges into the ectoflesh of his ass hard enough to puncture and draw blood. Sans couldn’t endure another moment of the twisted edgelord berating and manhandling him while shooting his hot load into his battered body, money or no money. “i’m not your brother. i’m not him. your brother is dead,” Sans shrieked. 

Edge froze though his cock continued to twitch and empty itself inside of the smaller skeleton. Sans instantly regretted his actions.

Shock turned to blind rage in the wake of Sans’ words. Edge practically threw Sans forward and off of his cock. Sans attempted to crawl away, but Edge grabbed him and flipped him onto his back. The expression on Edge’s angular face was terrifying to see. A miasma of red magic rose from the tall skeleton’s very bones.

Crimson tinted tears streamed down Edge’s cheeks; he roared like a mortally wounded beast. Sans started to apologize, hoping to diffuse the situation, but Edge struck him across the face. “HOW. DARE. YOU,” Edge bellowed, fist connecting with Sans’ face once, twice, thrice in quick succession.

Madness blazed from Edge’s crimson eyelights. Sans winced, expecting more blows at any moment, but nothing happened. Sans opened a socket to peek at Edge just in time to see the scarred skeleton standing between his spread legs, hand still balled into a fist. Edge wasn’t about to hit him again though.

“no, don’t-”

Edge slammed his fist into Sans’ pussy up to the elbow. Sans screamed and screamed. The pain was so excruciating that he couldn’t move, couldn’t hear, couldn’t see, couldn’t even feel anything except Edge’s fist pumping in and out of him, forcing its way past his cervix to violate his womb. 

Everything went white, then blissfully black as unconsciousness washed over Sans.

* * *

 

Sans gradually awoke to find Edge looming over him, looking, if anything, more insane than he had before. Edge idly twirled a sharpened bone attack in one hand, watching Sans sleep and eventually regain consciousness with an eerie hyper-focus.

Ropes bound Sans’ wrists to the headboard, but the basketball shorts he wore had been pulled up to cover his pelvis. Thank the stars for small mercies, thought Sans. He solemnly swore to give up prostituting for good after this. If Edge would only untie him….

“I MUST APOLOGIZE FOR BEING SO HARD ON YOU, BROTHER,” Edge said softly.

“look, pal, i’m not-”

“NOT MY BROTHER. I REALIZE THAT NOW,” Edge said contritely. “MY DEAR BROTHER LIVED A DANGEROUS LIFE THAT LEFT HIM SCARRED, AND YOUR BONES ARE PRISTINE…”

Sans relaxed, reassured that Edge had seen the error of his ways. 

“...BUT THAT CAN BE EASILY REMEDIED.”

Edge lowered the point of his bone attack to Sans’ radius, his maniacal laughter drowning out Sans’ screams as he carved familiar patterns into the surrogate bones.


	10. Day Nine: Edgeberry (Titfucking, Sthenolagnia (Strength/Muscles), Lingerie

**Summary for the Chapter:**

> Pairing: US!Sans x UF!Papyrus (Edgeberry)
> 
> Featured Kinks: Titfucking, Sthenolagnia (Strength/Muscles), Lingerie
> 
> Additional Warnings: Semi-public sex

Edge couldn’t stop staring. He had complained on the entire trip to the beach. He’d refused to go anywhere near the water. He’d scowled and groaned at the easy companionship and laughter of the other monsters who had invited him and Red on this ridiculous trip. Now he was grateful that he hadn’t stayed home because Blue had just shed his t-shirt to reveal the hottest ecto-body Edge had ever laid eyelights on.

He knew Blue worked out; they actually trained together. Edge never saw Blue without his flimsy, pathetic battle body though, a fact which he now regretted. The scarred skeleton’s hands itched to glide up and down those rippling abs. He wanted to caress the bulging biceps. He wanted to let his hands slide lower to see what else he’d been missing out on. Edge wondered if Blue needed help applying sunscreen.

Blue noticed Edge’s longing gaze and mistook it for a sign of loneliness. He bounded over to the beach chair where Edge sat like a friendly dog seeing his owner for the first time after a long absence. Grabbing Edge’s hand and giggling, Blue pulled him up out of the chair and towards the playfully lapping waves.

“C’mon, Edge! There’s No Reason To Be Grumpy On Such A Beautiful Day! Come Swim With Us!” Blue coaxed.

Edge allowed Blue to lead him right up to the edge of the wet sand, watching the smaller skeleton’s toned muscles flex as he moved. The pale blue ecto-flesh glistened under the bright golden rays of the sun, still wet from swimming and splashing, and Edge sighed heavily. As much as he would enjoy wrestling in the gentle waves with Blue, he was woefully unprepared.

“I Did Not Bring Swimwear,” Edge grumbled. He’d planned to sulk during the entirety of the day trip, not enjoy himself.

“Never Fear, Edgy Me! I Brought An Extra Suit, And We Are The Same Size,” offered Papyrus, always the helpful friend.

An energetic Blue darted past Edge on the way back to their beach gear. By the time Edge arrived, Blue had already dragged a flattering one-piece out of Papyrus’ oversized beach bag. The swimsuit would definitely fit him, but it wouldn’t leave much to the imagination. When the effervescent little skeleton handed him the suit, Edge accepted it. He didn’t mind showing off his slim physique.

“There Are Changing Rooms Over There,” said Blue, pointing to a row of booths with slatted wooden doors further down the beach. None of the changing rooms were occupied, so Edge slipped into the nearest one, swimsuit in hand, and began to remove his clothing. He stripped off his plain black t-shirt and black stone-washed jeans, standing in the center of the small space in just a lacy black bra and panties, looking for somewhere to set his clothing.

Blue’s skull popped in to continue his incessant chatter.

“I Forgot To Tell You-” Blue’s words trailed off, and his sockets widened. “Are You… Wearing Lingerie?” he asked, slipping into the changing room with Edge and pushing the door closed behind him. The shorter skeleton’s normally innocent blue eyelights smoldered with desire as they raked Edge’s every curve. 

“Lingerie? Of Course Not! I Simply Chose The Undergarments Most Befitting My Greatness,” Edge declared loftily, remembering the day that he had purchased the matched set. He rarely bought or wore such delicate articles of clothing, but when he saw the dark purple satin and black lace overlay on the bra and panty set in the display window of a lingerie shop, he knew he had to have it. It had been worth every penny to have Blue admire him so openly.

“It Suits You,” Blue murmured, voice low and sultry. His body nearly brushed Edge’s in the confined space, and the taller skeleton’s breath hitched at his proximity. Blue’s fingers traced the frills of lace along Edge’s pantyline, and a soft blue glow lit the small space, emanating from Blue’s swim trunks.

The way the fabric tented indicated that Blue’s summoned cock was equally as brawny as his muscles, and Edge’s mouth watered to have a taste. It didn’t help that the phalanges on one of Blue’s hands were enthusiastically exploring the inside of his panties. The other hand traveled upwards, caressing his side and eventually cupping one of his modest breasts.

Blue maintained eye contact with the scarred skeleton as he ran his fingertips over the scalloped upper edge of the bra. “You Know,” he purred sensually, “This Would Look Even Better  _Off_.”

Like a pair of dancers performing a choreographed and much-practiced routine, Edge’s hands infiltrated Blue’s shorts, pushing them down off of his hips and revealing an impressive throbbing erection. Blue hands found their way to Edge’s shoulders, fingers tangling in his lacy bra straps and shoving them aside. Blue tugged the front of the Edge’s bra down to expose the soft mounds of his breasts, simultaneously guiding the taller skeleton into a kneeling position.

Edge opened his mouth, extending the dark crimson magic of his tongue to lap at Blue’s cock, but the shorter skeleton stopped him. “Not Your Mouth, Edge. I Want To Feel Your Tits Around My Cock,” Blue whispered, eyelights trained on Edge’s perky nipples, mesmerized and breathing heavily.

Blue rested his warm shaft between Edge’s breasts while the taller skeleton slowly caressed them, rolling his sensitive nipples between his phalanges. Blue rested his hands on Edge’s skull and leaned back against the wooden door of the changing room, and Edge pressed his tits together, rocking his body as he rubbed the supple flesh along Blue’s length, making them both moan.

* * *

“It Sure Is Taking Edgy Me A Long Time To Change! He And Blue Are Missing Out On The Fun!” commented Papyrus, tossing a brightly-colored beach ball from hand to hand while he decided who to throw it to.

Stretch could see the door of the changing room shaking on its hinges from where he floated, sprawled out on an inner tube. “i think they’re having plenty of fun by themselves,” he chuckled under his breath.


	11. Day Ten: UT!Sans x HT!Papyrus (Micro/Macro, Bonds (Telepathic and Empathic))

**Summary for the Chapter:**

> Pairing: UT!Sans x HT!Papyrus
> 
> Featured Kinks: Micro/Macro, Bonds (Telepathic or Empathic)
> 
> Additional Warnings: Emeto/Vomit (of cum), Dislocation/Injury, Collaring, Heat Cycle
> 
> NOTE: I am aware that this ship isn’t exactly Micro/Macro. It is more of an extreme size difference.

The Papyrus who escaped the hardships of Horrortale was gigantic compared to his counterparts, and unlike most Papyruses, he rarely spoke. Unusually long limbs, sunken sockets, and crooked, blood-stained teeth gave him a nightmarish appearance that few could stomach. Humans and monsters alike feared the strange, hunched creature, but Sans felt nothing except sympathy for this skeleton who was so like yet so unlike his own brother.

Sans worried that frightened citizens might form some sort of mob to drive the oversized skeleton out of town, so he invited the hulking skeleton monster to live with him. In a flash of inspiration, Sans also bought a thick leather collar to present to the unusual Papyrus, whom everyone referred to as Crooks. The thick leather served multiple purposes, all designed to keep Crooks safe.

The royal blue leather- the same color as Sans’ magic- rested across Crooks’ throat in the exact spot where an assailant might attempt to behead him. Sans often had nightmares about Crooks dying by decapitation, and the placement of the collar eased his anxious mind. Other monsters and humans recognized the collar as a sign that Sans was responsible for Crooks, and they accepted that Sans would keep the massive skeleton under control.

Most importantly, the collar reassured Crooks that Sans would take care of him. Despite his intimidating looks, disapproval and aggression terrified the gentle giant. Crooks craved acceptance even more than he craved food, and that said a lot about his personality. Yes, Crooks definitely reminded Sans of his own brother back when Papyrus had needed him, before he moved out and started a life of his own… a life that did not include Sans..

Sans swore to tend to his stand-in brother’s every need, and he didn’t make promises lightly. His determination was put to the test soon enough when Crooks went into heat. The intense drive to mate took over his mind and body entirely, and poor Crooks couldn’t control himself. Sans refused to risk Crooks attacking or injuring someone, so he decided to relieve the huge monster’s heat in the privacy of their home. After all, he could handle a little size difference, right?

The sight of Crooks’ thick, hard cock gave the small skeleton immediate second thoughts. Would it even fit? Crooks whimpered; his body ached for any kind of stimulation to relieve the scorching lust making his bones itch and and throb. Sighing, Sans stripped down. He barely had a chance to summon anything before Crooks pounced, pinning him flat on his stomach on the floor.

Sans’ magic swirled and formed into a pussy around the oversized cock already invading his pelvic inlet. Sans gritted his teeth. He hadn’t expected foreplay under these circumstances, but Crooks’ cock was just too big. His magic could barely stretch to accommodate it. With a sickening CLICK, Crooks sank into Sans’ pussy to the base, dislocating Sans’ pubic symphysis in the process.

All Sans could do was desperately cling to consciousness and sanity while Crooks used his body for his own sexual release. The blood red cock pounding into him filled him all the way into his ribcage as if he were nothing more than a bony cocksleeve. _Ribbed for his pleasure,_ thought Sans, bordering on hysterical. He knew Crooks didn’t mean to hurt him, but his magic struggled to hold together during the rough fucking, and every tear made him want to beg for mercy.

Crooks slammed Sans down on his cock with firm finality. Sans could feel the huge cock pulsing inside of him, ready to release its load. When Crooks came, Sans’ magic tore apart completely. Sans tipped forward to sprawl across Crooks’ ribcage. He opened his mouth to scream at the sensation of foreign magic filling up his entire body, but all that came out was a flood of blood red cum.

The smaller skeleton flopped limply in Crooks’ grasp. He hoped Crooks’ heat was satisfied, but he seriously doubted it. Surely Crooks wouldn’t fuck him until he dusted. He held onto that sliver of hope as Crooks’ hips began to buck once more.


	12. Day Eleven: Cherryberry (Object Insertion, Sounding, Cross-dressing)

**Summary for the Chapter:**

> Pairing: US!Sans x UF!Sans (Cherryberry)
> 
> Featured Kinks: Object Insertion, Sounding, Cross-dressing
> 
> Additional Warnings: Roleplay, Cum Eating

Red hated losing bets. He especially hated losing bets when the payout involved him dressing in a sexy maid outfit and cleaning his friend Stretch’s house, and that smug, smiling bastard Blue’s presence was just infuriating icing on the humiliation cake. The bossy little neat freak had been micro-managing him the entire fucking day!

“YOU MISSED A SPOT,” Blue declared, pointing towards the sofa.

“where?” growled Red.

“UNDER THE SOFA,” Blue said innocently.

“how could i have missed a spot under the sofa when i didn’t even clean under the sofa?” Red’s voice rose with each word until he was shouting and waving his arms in agitation, but Blue simply smirked.

“EXACTLY.”

Grumbling mutinously, Red got on his hands and knees and bent forward to sweep beneath the sofa with his feather duster. How do you make a mess under your furniture? Red suspected that Blue just wanted to see him squirm, and Blue only confirmed those suspicions, tilting his head sideways to get a better view right up Red’s frilly maid skirt.

Stretch had really gone all-out on the maid outfit. The panties were the same black, white, and frills pattern as the off the shoulder, extremely short dress, and peeking out over the top edge of the panties was Red’s hard cock. He must like the feel of satin against his ecto-flesh, mused Blue, admiring the length of Red’s shaft.

Blue tugged at Red’s panties while the irritable skeleton focused on his work. Blue used the fabric to pull Red backwards across the floor and away from the couch, then he flipped Red onto his back and crawled forward between Red’s legs, lifting the skirt to see Red’s cock sticking out of his panties from a different angle.

“hey!” shouted Red, trying to cover himself with the meager fabric of his skirt with one hand and smacking Blue with the feather duster in the other. “quit bein’ a perv!”

“DO YOU REALLY WANT ME TO STOP, RED? BECAUSE YOUR SWEET LITTLE COCK LOOKS LIKE IT COULD USE SOME ATTENTION,” purred Blue, dragging Red’s panties down and letting his cock bob free. A bead of pre-cum formed at the tip, and Blue thumbed at it teasingly.

Red’s hips bucked automatically, seeking more stimulation. “fine, but this excuses me from any more cleaning!”

“YOU’LL BE MUCH TOO TIRED TO CLEAN WHEN I’M DONE WITH YOU.” Blue laughed maniacally, and Red hoped that he wouldn’t regret their deal.

With a wicked and not at all comforting smile on his cherubic face, Blue summoned a glowing orange bone attack. The bone was small and came to a narrow point at one end. Blue twirled the tiny bone. Red watched him, wondering what he needed such an insignificant bone attack for.

“REMEMBER, WITH ORANGE ATTACKS YOU HAVE TO KEEP MOVING.”

Was Blue giving him a battle lesson? Red’s cock twitched in frustration. Blue could be so damn infuriating. Red opened his mouth to complain, but Blue cut him off by shoving the little orange bone into his urethra. Red gasped and groaned, but it sounded more like a moan of pleasure than a cry of pain.

The shock took a moment to wear off, and to prevent Red from being injured- or worse, dusted- Blue squeezed and stroked his cock vigorously. Once Red’s eyelights refocused, Blue guided Red’s hand to his own shaft. “KEEP MOVING,” Blue instructed him.

Red pumped his cock in earnest, and Blue watched him with hungry eyes. Red couldn’t slow down because of the orange color of the bone, but it also prevented him from cumming. At first he didn’t mind, but after jerking it for what felt like an eternity, the inability to cum became maddening. His toes curled, and his back arched, but nothing relieved the tension in his balls, that intense, bordering on painful, need to cum.

Blue monitored the situation carefully. He watched pleasure turn to annoyance, then to desperation on Red’s face. The other skeleton’s cock was swollen and throbbing with the built up pressure, but there wasn’t anywhere for it to go. Reaching down, Blue grabbed the bone attack, pumped it in and out of Red’s urethra a few extra times, then yanked it out.

Red’s entire body jerked and thrashed as cum shot out of his cock in thick, sticky strands.

With his cock now emptied all over the freshly vacuumed carpet, Red leaned back and closed his sockets. His breathing came in heavy pants, and when Blue nudged him, he didn’t move at first. Blue nudged his sensitive cum-coated cock again, and Red opened one baleful socket.

“whaddaya want now?” he snapped.

“MAKE A PUSSY FOR ME.”

“how about i don’t?” offered the cantankerous skeleton monster.

“I GUESS YOU’LL BE CLEANING THE SHED THEN,” Blue chirped flippantly. “IT HASN’T BEEN CLEANED IN YEARS, AND STRETCH REFUSES TO DO IT.”

“ugh, fine. anything to avoid more cleaning.”

Red sighed in an exaggerated and long-suffering way and dismissed his cock only to manifest a lovely little pussy in its place. Blue’s fingers immediately began probing it, spreading the smooth puffy lips and exploring the silky inner folds. Arousal already slicked Red’s entrance, and Blue’s expert ministrations had him soaking in seconds.

“GET ON YOUR HANDS AND KNEES,” Blue ordered, voice husky with desire. He licked Red’s juices off of his fingers, humming at the tangy flavor.

“what are you going to do?”Red narrowed his sockets and glared, not trusting Blue one bit.

“I JUST WANT TO PLAY WITH YOU, RED. I’LL MAKE YOU FEEL SO GOOD.”

Red couldn’t resist Blue’s offer. He’d have to be a complete idiot to turn down sex in favor of doing chores. He didn’t even do chores in his own universe! Red took up the requested position, and Blue moved behind him. Something smooth, hard, and round rubbed along his slit, and Red knew that it wasn’t Blue’s fingers or cock. The little shit was using another bone attack on him!

“hey-” Red yelled over his shoulder, but he never got the chance to utter another word because the long bone started to slip into his tight cunt, and the sensation left him speechless. Blue pulled the bone back out and then shoved it in farther. The bulbous end of the bone filled his sensitive pussy deliciously, and the length of the bone meant that it penetrated deeply with every thrust.

“NOW CLEAN UP YOUR MESS.” Blue removed the bone from Red’s needy cunt and rubbed it against his clit.

“wait, what? don’t stop Blue…” Red’s words came out on ragged breaths.

“LICK YOUR CUM OFF OF THE CARPET, RED.”

Red obediently lowered his face to the ugly zig-zag striped living room carpet and scooped up some of his cum with his tongue.

“GOOD BOY. JUST LIKE THAT,” encouraged Blue, slamming the bone attack back into Red’s empty cunt. Red mewled loudly at the sudden fullness. He never expected that he would enjoy being fucked with an actual bone despite his many puns to that effect.

Blue set a fast, rough pace, and his bone attack pounded Red’s pussy raw as he lapped up his own cum. Blue didn’t even slow down when Red came the first time. Or the second time. Or the third…

* * *

Stretch checked in on his brother and his friend later that night. Blue sat on the couch, flipping through channels, looking for an NTT special to watch. Red was curled up in Blue’s lap with a blanket wrapped around him, and Blue absently petted his skull with one hand. Red’s closed sockets and even breathing indicated that he’d fallen asleep.

“sexually harassing the help?” asked Stretch.

“IT WAS CONSENSUAL,” protested Blue.

“don’t worry, bro, i’m just teasing.” Blue huffed at his brother’s statement, but he couldn’t be mad at Stretch.

“THANKS FOR WINNING THAT BET FOR ME, PAPY. THE SEXY MAID OUTFIT WAS A NICE TOUCH.”

“anything for you, bro, but next time… maybe just tell him how you feel?”

“NAH. IT’S MORE FUN THIS WAY,” Blue giggled.


	13. Day Twelve: HT!Sans x Reader

**Summary for the Chapter:**

> Pairing: HT!Sans x Reader
> 
> Featured Kinks: Licking, Petplay
> 
> Additional Warnings: Sex Toys (Anal), Gender Neutral Reader

The smooth vinyl catsuit hugged every inch of your body tightly with openings only for your head and ass; you felt the pressure of the butt plug anchoring your tail spreading your asshole, igniting little jolts of pleasure in you every time you moved. You regretted that your cat ears were stiff and immobile, but as long as your Master approved of your attire, you were happy.

Speaking of your Master…

“come here, kitty cat,” Master’s voice rumbled from the living room, and you scurried to his location like a good pet. You found him lounging on the sofa, legs spread casually. He wore a clean shirt today, one without bloodstains. You averted your eyes from the hole in his skull just as he’d told you to do when he first put the blood red leather collar around your neck. You always obeyed him.

Obedient pets received rewards.

You crawled towards him on your hands and knees, nuzzling his legs affectionately. When he patted your head gently and let his hand trail along the side of your face, you nearly wiggled with joy. You managed to behave yourself though. You always tried to be a good pet for Master in hopes of receiving his rare but genuine praise.

“that’s a good kitty,” said the skeleton monster who owned you. You sat attentively in front of him, basking in the comfort and familiarity of his deep, growly voice.

“open your mouth for me, pet,” he ordered without raising his voice. He never commanded or scolded you by yelling, and his voice was like a caress to your often frazzled nerves. Master took care of you. Master made the decisions. Master rewarded good behavior and corrected bad behavior fairly. You would do anything for him.

You opened your mouth, letting him stick his fingers inside. He captured your tongue between two thick phalanges and pulled it out slightly, inspecting it with a soft “hmm.” He must have liked what he saw because he released your tongue, leaned back, and spoke the words you always eagerly waited to hear.

“you’ve been such a good pet. come get your treat, kitty.” Master gestured to the obvious outline of an erection glowing a deep burgundy in his shorts. You dutifully crept forward, and with reverent hands, pulled the waistband of his shorts down to expose Master’s beautiful blood red cock.

Master kept murmuring what a good kitty you were. He stroked your head as you lowered your mouth over his cock, careful not to dislodge your ears. You wanted to do the very best job you could for your Master, so your wrapped one of your hands around the base of his cock, squeezing and pumping it while you lapped at the underside with your tongue.

You listened to Master’s ragged panting to gauge how well you were performing your task. He especially enjoyed the feeling of your warm wet tongue sliding up and down the length of his cock and leaving a glistening trail of saliva in its wake, so you decided to do more of that. Anything to please your Master and perhaps earn a special reward.

Flattening your tongue, you licked the underside of Master’s shaft once more, swirling your tongue around the tip to taste the precum that gathered there. Your hand continued its up and down motions, and you could feel the building heat of your Master’s pleasure warming your hand. You hummed to send vibrations through the blood red magic, and Master’s cock throbbed in response.

“so close, kitten… just a little more…” the skeleton monster gasped, sending shivers down your spine. Your hand moved faster and faster, and you licked with quick, hard strokes, encouraging Master’s thick length to swell with cum.

Master’s hand stilled atop your head, and his skull lolled back. Pushing you away slightly, Master positioned you in front of him just in time for the first hot, sticky strands of his cum to land on your face. You continued to milk his cock, taking it all on your face, just the way Master preferred it. It felt so good to be marked by Master’s cum.

“be a good kitty and lick me clean,” Master instructed, “then go to my bedroom, and i’ll give you your reward.”

You nodded, already licking up the cum coating Master’s still-hard cock and shorts. Whatever Master wanted, you would do without question.

_Obedient pets received rewards._


	14. Day Thirteen: Mythtale UT!Bros x Mythtale US!Bros (Distant/Distracted Sex, Creampie)

**Summary for the Chapter:**

> Pairing: Mythtale UT!bros x Mythtale US!bros
> 
> Featured Kinks: Distant/Distracted Sex, Creampie
> 
> Additional Warnings: Mythtale fontcest, centaur/horse cock, cum inflation, double penetration, knotting, heat cycle
> 
> NOTE: Mythtale by mythtale / mellednsfw (on Tumblr). Mythtale UT!Sans and UT!Papyrus are an angel and a centaur. Mythtale US!Sans and US!Papyrus are a faerie and a kitsune.

Blue the faerie and his kitsune companion, Stretch, crested a hill overlooking a monastery and nearby stable. The gates of the monastery were closed for the evening, but the ever-optimistic faerie pointed to the lantern light still visible from the stable.

“WE COULD STAY IN THE STABLE OVERNIGHT AND VISIT THE MONASTERY TOMORROW,” suggested Blue to a very tired Stretch. The pair had travelled all day, and the kitsune didn’t care if they slept on jagged rocks as long as they would be off of their feet. Stretch envied Blue’s butterfly wings and gift of flight on journeys like there.

“sounds good, Blue,” Stretch agreed.

As the faerie and kitsune neared the stable, they heard voices engaged in low, barely audible conversation. Curious, the two travellers pressed their skulls against the side of the barn to hear what was being discussed. The kitsune especially never passed up on an opportunity to gather what might be valuable information.

“-don’t mind helping you out, Paps,” said one speaker.

“But You’re An Angel,” protested a second speaker.

“aren’t angels supposed to assist mortals?” The first speaker spoke again.

“I Don’t Think That Includes Mating, Sans,” said the second speaker uncertainly.

Mating? Angels? Blue and Stretch exchanged a look. No way could they resist further eavesdropping after hearing that particular snippet of conversation. Sneaking around to the barn doors, Blue slowly pushed them open just enough for him and Stretch to slip inside. They crept forward towards the source of the voices- the very last stall in the stable. What a strange place for a tryst!

Crouching just outside of the sphere of light cast by the lanterns, the duo listened to the continuing conversation with unwavering attention.

“-might get mad if i make something as elaborate as last time,” said Speaker One.

“You Won’t Enjoy It If You Don’t Put Some Effort Into Making Your… Parts… Though,” Voice Two pointed out.

“don’t worry about it, Paps. this is about relieving your heat. i’ll be fine.”

Noisy thuds came from the stall as if heavy objects were being dropped or tossed around. The voices sounded perfectly normal despite the strange topic, but the sounds coming from the stable didn’t match the scenario that Blue and Stretch imagined. They needed to investigate further! Fortunately, the faerie and the kitsune were masters of espionage, able to move in silence and disappear like shadows in the night.

Staying low to the ground, the kitsune cautiously peeked around the corner into the occupied stall. Blue joined him, slipping under Stretch’s arms in a way that pressed his round ass firmly (and distractingly) against the kitsune’s crotch. Stretch’s magic stirred in response, but the sight before his sockets prevented him from tossing Blue into the hay for some barnyard sex shenanigans.

The kitsune didn’t know what he expected. There  _was_  an angel in the stall, complete with golden halo and wings of purest white… but the second speaker turned out to be a skeleton centaur, and he was currently railing the angel hard into the hay. Unperturbed, the angel relaxed between the centaur’s front hooves while the massive horse cock pounded away at him, its outline clearly visible in the bulge of his stomach.

“Are You Alright, Sans? I’m Not Hurting You, Am I?” The centaur asked, worried about his partner who looked like he might burst at any moment.

“nah, i’m virtually indestructible, so do what you gotta do, Paps,” the angel reassured the centaur.

Stretch wanted to rub his sockets in disbelief, but he resisted the urge to avoid drawing attention to himself and Blue. If the centaur’s ragged breathing and hastily moaned words were anything to go by, the salacious act would be finished soon enough anyway.

“I’m… I’m So Close, Sans… May I Please-”

“HI!”

Before Stretch could stop him, Blue darted out into the light to introduce himself to the two skeleton monsters, mid-copulation. Stretch made a grab for his companion, but Blue dodged, leaving the kitsune to fall flat on his face on the floor, almost eye-to-eye with the nonchalant angel.

“Hello There, Small Friend And, Erm, Fox Monster,” the centaur greeted them automatically. Manners were important to a future noble knight, even a future noble knight who was currently having sex in a barn with an angel.

“HE’S A KITSUNE,” chirped Blue, seemingly oblivious to the fact that the embarrassed centaur was using the angel’s entire body to attempt to conceal his exposed cock. The angel, still unconcerned, allowed himself to be handled like a ragdoll by his partner.

“ARE YOU REALLY IN HEAT, MR. CENTAUR?” Blue asked innocently, sidling closer to get a better view of the horse cock visible through the angel’s blue ecto-flesh. The angel’s stomach could barely contain it because of its enormous size! Blue wanted that cock inside of him badly, and his magic reacted. “I COULD HELP YOU WITH THAT IF YOU WANT,” he offered breathlessly.

“Blue, he literally already has his dick in someone,” Stretch objected weakly.

Stretch knew what Blue intended to do, and he also knew that there was no stopping Blue when he set his mind to something, so he let the scenario unfold without further protest. He and the faerie shared an open relationship, and Stretch didn’t mind a bit of voyeurism if the other two skeletons agreed to it. The kitsune rocked back on his heels while Blue worked the magic of his charm.

“that’s ok,” the angel said with a wink that belied the compromising position he was in. “let the faerie have a turn if he wants. as long as Paps is ok with it.” Blue turn his back on the skeleton angel and centaur and yanked down his hose to present Paps with his soaking wet pussy. The centaur surreptitiously sniffed, inhaling the scent of Blue’s arousal.

The strange turn of events left the centaur speechless for a few moments before he finally recovered himself. “I… Would Not Mind. Anything To Relieve My Heat. It Is Nearly Unbearable.” He neglected to mention that the sight and scent of Blue’s delectable pussy was driving him wild with lust.

The centaur pulled out of Sans’ hastily slapped together, barely anatomically accurate pussy in favor of Blue’s luscious mound, but he did have one very real concern regarding the faerie’s very small frame: “Is It Going To Fit? I Don’t Want To Injure You.”

“THEN ALLOW ME TO TAKE THE LEAD,” Blue offered confidently, gently shoving the centaur down so that he partially reclined against a hay bale. The faerie straddled Papyrus’ hips like a very confused upside-down cowboy and lined up his pussy with the tip of the centaur’s huge cock.

The pair of spectators watched in awe as Blue worked himself into a lather with his fingers and used his glistening arousal lube up Papyrus’ shaft. The faerie spread himself with two finger and guided the head of the mighty horse cock into his eagerly palpitating pussy. Blue’s eyelights morphed into stars the moment the horse cock entered him. This was a dream come true for the insatiable size queen.

Blue lowered himself slowly, inch by inch onto Papyrus’ cock, but the centaur’s heat melted away all of his patience. The skeleton centaur gave Blue an apologetic look then grabbed his hips and shove him down onto the last few inches of his aching shaft. Blue mewled with pleasure, eyelights rolling back into his head and tongue flopping loosely out of his mouth, taken over completely by pleasure.

Fully seated at last, the centaur’s thick length stretched Blue’s magic to the limit, and he loved it. He craved that overfilled feeling and marveled at the outline of Papyrus’ shaft pushing outwards from the magic of his stomach. Leaning forward for the best angle, Blue began to move, taking his time to adjust at first, then lifting himself up and slamming himself down faster and faster.

Sans watched the proceedings with his usual indifference, but Stretch couldn’t help rubbing at his pelvis and summoning his own cock as he watched Blue ride the horse-sized shaft in front of him. When Blue bent forward, exposing his tight little asshole, Stretch stopped holding back. He cast aside his kimono, stepped forward, and rutted against Blue’s round asscheeks.

“do you mind if i join you two?” he asked unnecessarily. Papyrus was lost to the pleasure of fucking Blue’s tight, clenching pussy, and Blue was already spreading his ass to take his boyfriend’s cock down to the rapidly swelling knot.

Blue mewled and moaned as the two thick cocks destroyed both of his holes in euphoric tandem. Each time Stretch hilted, eventually managing to get his knot inside of the faerie’s asshole, Blue lifted himself entirely off of Papyrus, and when Blue took all of Papyrus, Stretch withdrew only slam in again harder the next time.

Blue’s sockets widened as both cocks plunged into him at the same time. Cum, more cum than he ever imagined, spilled into his stomach and uterus. His insides were hot, so hot, so full, and the faerie rode out his own orgasm on waves of exquisite bliss. He barely noticed when Stretch and Papyrus helped him off of their cocks and laid him down on a soft bed of hay.

Blue gazed down at the two shades of cum swirling in the swollen magic of his stomach. There was so much cum that he couldn’t dismiss his ecto-body. All he could do was stare with half-lidded socket and heart-shaped eyelights at the mess flowing out of him. It almost felt as good dripping out of his pussy and asshole as it had going in.

Papyrus and Stretch both rubbed and carefully pressed Blue’s distended stomach, admiring their handiwork and marveling at the amount of cum inside of the faerie’s small body. Dozing off from the harrowing sex session, Blue murmured a parting comment:

“I HOPE YOUR HEAT ISN’T OVER YET, MR. CENTAUR. I’D LIKE TO GO AGAIN.”

Stretch sputtered at Blue’s audacity, but Papyrus merely nodded.

“It’s Only Just Begun.”


	15. Day Fourteen: Nightmare x Error (Asphyxiation, Cunnilingus, Distension, Tentacles)

**Summary for the Chapter:**

> Pairing: Nightmare x Error
> 
> Featured Kinks: Asphyxiation, Cunnilingus, Distension, Tentacles
> 
> Additional Warnings: CONTAINS NON-CON, bondage

“I think maybe you need to be reminded who’s the boss around here, glitch,” growled Nightmare. Error struggled in the grip of the slimy tentacles that held him, his own weapon- blue strings that enabled him to manipulate other monsters- rendered useless by the writhing appendages springing from the back of the perpetually oozing skeleton in front of him.

“Don’t- don’t touch me!” shrieked Error, but Nightmare only chuckled.

“I’m going to do more than touch you…” Nightmare prowled forward, and Error could do nothing to stop him.

Wrapping one tentacle tightly around Error’s wrists, Nightmare lifted the other skeleton off of his feet entirely, letting his subordinate dangle helplessly by the arms while his other tentacles crept up Error’s body, tearing away his clothing and revealing the yellow, red, and black bones underneath. Nothing screamed dominance quite like humiliating your enemy completely before putting him in his place.

Two more tentacles fastened themselves around each of Error’s femurs, spreading his legs wide and exposing the pussy that had manifested in Error’s pelvis during his rough handling by Nightmare. The sludge-seeping skeleton leaned in close to investigate the silky folds  and dribbling opening within.

“No! Stop-!” Nightmare cut off Error’s protests by encircling his neck with yet another tentacle and squeezing until the other skeleton’s air supply was cut off completely. That should silence the pathetic glitch’s incessant babbling. With blissful peace and quiet instilled, Nightmare lowered his mouth to his struggling prey’s pussy.

The manifestation of negative energy that coated every part of Nightmare’s body served as a lubricant when his tongue delved in between Error’s pussy lips to taste his arousal. Error’s screams came out as gurgles with Nightmare’s tentacle choking him, but the screams turned into moans when Nightmare’s tongue finally slipped into his fluttering pussy.

Nightmare’s tongue darted in and out of Error’s tasty little cunt a few times before the tentacled skeleton moved away. Nightmare didn’t want to get distracted from the purpose of his visit. He wasn’t here for pleasure- his  _or_ Error’s. He was here to punish the insolent little glitch who refused to follow orders.

Using his thumbs to pry Error’s cunt open as far as he it would stretch, Nightmare grinned a nightmarish grin. A squirming mass of dripping tentacles exploded from Nightmare’s back, plunging into Error’s pussy and splitting it wide open. Error’s mismatched eyelights widened in fear and pain, and Nightmare loosening his asphyxiating tentacle to hear his victim scream and beg for mercy.

“No! No more! Stop! You’re tearing me apart!” Error babbled in a high-pitched shriek. His words trailed off into incomprehensible shrieks as Nightmare’s tentacles twisted and writhed inside of him, disfiguring his magic and causing his stomach to swell painfully with their movement.

“Tell me who is in charge around here, and I may grant your mercy,” hissed Nightmare, forcing more tentacles into Error’s body through his asshole to add to the distending array of oozing appendages violently penetrating his pussy. The goopy tentacles made wet slapping and squelching noises as they worked their way in and out of Error’s fuckholes, a symphony for a sadistic skeleton’s ear canals.

Error struggled to answer the question; he couldn’t focus with so many tentacles pounding his pussy and ass and uncurling in his stomach to stretch his magic nearly to the breaking point. Did Nightmare plan to kill him? It didn’t matter; he wouldn’t beg.

“Fuck you,” snarled Error.

Nightmare blinked in surprise, then sighed. Two more tentacles shot out of his back to slide down Error’s throat, cutting off any chance of further communication. Some subordinates never learned….


	16. Day Fifteen: Horrorcest (Over Stimulation, Intercrural Sex, Uniforms)

**Summary for the Chapter:**

> Pairing: HT!Sans x HT!Papyrus (Horrorcest, BloodSugar)
> 
> Featured Kinks: Overstimulation, Intercrural Sex, Uniforms
> 
> Additional Warnings: Fontcest/Horrorcest, Sex toys (Vaginal)
> 
> NOTE: This version of Horrortale belongs to redtomatofan on Tumblr

“Are you sure Blood will like my Halloween costume?” asked Sugar shyly.

“He’ll Love It,” Papyrus reassured him with his usual easy confidence, straightening the extremely short skirt of Sugar’s naughty nurse uniform so that it showed just the slightest curve of the underside of Sugar’s ass.  _Perfect_. “Did You Remember To Bring The Box I Gave You?”

Sugar held up a small cardboard box that had once contained a pair of brand new bullet vibrators. Now it only contained the wireless controllers and empty packaging. “Yes, and I put both of them in already,” he declared proudly.

Papyrus took the controllers and tucked them into the pockets of Sugar’s uniform. Smiling, he patted Sugar’s shoulder affectionately before escorting him downstairs to the skeletons-only party in the basement. “Go Get ‘Em,” he whispered under his breath, watching Sugar step nervously into the room where his brother and the other skeletons waited.

Blood’s jaw nearly hit the floor when he saw his brother sidle shyly into the room. Sugar loved wearing cute, fashionable outfits, and he looked absolutely precious in them. Tonight though, Sugar looked like sex incarnate. The naughty nurse outfit he’d chosen hugged and accentuated his subtle curves and left the tops of his breasts and his asscheeks barely covered. Blood was glad he’d worn a loose robe as part of his demon outfit; the rest of the guests didn’t need to know that he had a massive erection just from seeing his brother’s costume.

Sugar made his way around the room, engaging in friendly small talk here and there as he moved surreptitiously in Blood’s direction. Blood prowled through the crowd as if he were a predator on the hunt for something sweet. When the two skeletons finally came face-to-face, Sugar averted his gaze from Blood’s overwhelmingly hungry eyelights.

“Do you… like my outfit, brother?” Sugar asked, nervous of the answer despite the fact that Blood appeared ready to pounce on him and take him right there on the floor in front of their friends.

“Shugs, I would break every bone in my body just so you could nurse me back to health,” breathed Blood reverently. Sugar blushed a pale coral-colored blush at his brother’s flattering words.

“That’s not necessary,” Sugar murmured close to his brother’s skull so that nobody else could hear him, “but if you’d like to play doctor, meet me upstairs in 20 minutes.” Sugar stepped back into the crowd and vanished from Blood’s sight but not before tucking the two bullet controllers into his brother’s hands.

Blood stared at the remotes, dumbfounded. As the realization of what they were dawned on him, he wondered if he would be able to wait the full 20 minutes.

Sugar barely made it to the top of the stairs before he felt one of the bullets buzz to life in his pussy, and he fell to his knees from the sheer pleasure that coursed through his entire body from it. Unable to walk on his wobbly legs, Sugar crawled into the spare bedroom that Papyrus had offered him for the night.

Papyrus watched Sugar slink back up the stairs, blushing furiously. A few minutes later, Blood followed him. Papyrus nodded to himself and strode over to the stereo to crank up the volume on the music and give the two Horrortale skeletons some privacy. Most of the skeletons here would be retiring to guest rooms or their own homes in pairs soon anyway, but none of them were quite so easily flustered as sweet and gentle Sugar.

Blood stood in the doorway of the guest room as he switched the second remote he held from OFF to LOW. The stocky skeleton rubbed his pelvis through his robe as Sugar moaned and pawed at his soaked panties on the bed. When Sugar finally managed to peel the panties away from his perfect little pussy, Blood could actually see arousal flowing out of the beautiful coral magic that Sugar had summoned.

“Brother… ah… I didn’t know… it was… so intense,” Sugar gasped, fisting the bed sheets. Waves of lust washed over him as he stared at his brother. Sugar had never been so turned on in his entire life.

“oh, Shugs, they’re only set to LOW right now,” Blood purred teasingly. “maybe we should try the HIGH setting?”

Sugar braced himself, but nothing could prepare him for the blinding euphoria of having both bullet vibrators vibrating on HIGH inside of him and sending jolts of tingling pleasure straight to his lower abdomen. Sugar tensed. His toes curled; his spine arched. Pressure built and then released, causing Sugar’s pussy to clench and pulse, but the stimulation didn’t stop. Sugar orgasmed a second time before the afterglow from the first even had a chance to fade.

“fuck, Shug, you look gorgeous when you cum,” groaned Blood. He climbed onto the bed and hiked his robe up over his head, tossing it onto the floor. He’d gone commando for the party, and his dark red cock twitched in the open air.

Leaving the bullets inside of Sugar’s sensitive pussy, Blood nestled his cock between Sugar’s delicate pussy lips, pushed his brother’s thighs together, and began to rut with powerful thrusts of his hips. The warm, smooth ecto-flesh of Sugar’s thighs felt amazing around his cock, and Sugar mewled and bucked his hips every time the tip of Blood’s cock skated over his swollen clit.

Soon, both skeleton’s were panting as their bodies rocked together.

Sugar came again. This time a gush of hot fluids squirted from his pussy onto Blood’s cock. Blood paused, breathing heavily and admiring the sticky cum still flowing out of Sugar. Sugar screamed as yet another orgasm rocked him. The buzzing of the vibrators against his tender walls after so many orgasms was bordering on painful, but somehow, Sugar didn’t want it to stop.

He wanted  _more_.

_He wanted his brother._

“Brother… brother, please… take me…  _fuck me_ ,” begged Sugar, body spasming from the overstimulation.  

Blood never had been one to disobey a nurse’s orders.


	17. Day Sixteen: HoneyMustard (Nipple Play, Frottage, Body Worship, Sixty-Nine)

**Summary for the Chapter:**

> Pairing: US!Papyrus x UF!Sans (HoneyMustard)
> 
> Featured Kinks: Nipple Play, Frottage, Body Worship, Sixty-Nine
> 
> Additional Warnings: None

“i don’t see what all the fuss is about,” murmured Stretch, nibbling at his boyfriend, Red’s clavicle.

“you need to get your vision checked then, dumbass. i’m covered in fucking scars,” hissed Red, trying unsuccessfully to pull away from his lover. Mashing a hand against Stretch’s face, Red shoved hard, but his obstinate boyfriend refused to give up his affectionate advances.

“so? just because you have scars doesn’t mean you aren’t gorgeous,” Stretch pointed out. A cherry red blush spread across Red’s cheekbones. Stretch pinched one of the unyielding bone cheeks teasingly. “just look at these cute little blushy cheeks!”

“stop it,” snapped Red, though his tone was more flustered than harsh. He slapped Stretch’s hand away, but deep in his SOUL, those words meant the world to him.

This was the first time Stretch had seen him fully naked. Usually when they had sex, Red lowered his shorts just enough to give the lanky skeleton access, then tugged them back up as soon as they were finished. He feared Stretch’s rejection if the other skeleton saw his disfigured body, nearly every bone criss-crossed with cracks and scars.

Red never expected this reaction.

“i’m just getting started,” declared Stretch loftily. “your magic is the most beautiful shade of candy apple red i’ve ever seen. you have amazingly strong and durable bones to have survived so much hardship, and somehow, after all of that, you still manage to have these elegant clavicles, gracefully sweeping ribs, and exquisite iliac crests.”

Stretch’s hands stroked each bone as he complimented it. His sensual touches and husky drawl caused Red’s acto-body to manifest, and Stretch’s sockets widened in surprise before narrowing to devilish slits. Red, it seemed, had been hiding a pair of full, luscious breasts underneath his oversized sweater!

“hey, go easy on the nip-” Red’s warning quickly became a yelp when Stretch’s mouth descended on one of the nipples in question. He yelped again when Stretch used one hand to give attention to the other nipple. Red’s nipples were extremely sensitive, and Stretch wasn’t going to go easy on them.

One nipple, Stretch rolled between his thumb and forefinger; the other, he nipped and suckled roughly. Stretch tugged one nipple while he licked the other, then he switched breasts to give them equal attention from his hand and mouth. Red writhed and screeched from the overwhelming pleasure, but he made no further effort to stop Stretch. It felt too good to stop.

Without removing his underwear, Stretch began to grind his erection against Red’s pussy. He kneaded Red’s breasts and captured Red’s mouth in a passionate kiss full of moaning and tongues before guiding his boyfriend’s hands down to his waistband so that Red could remove the unwanted and, at this point, unnecessary article of clothing himself.

Willing and eager, Red pawed his boyfriend’s underwear down and off, casting them aside. Stretch kept grinding his cock along Red’s arousal-slicked slit, and his phalanges tugged rhythmically at Red’s already painfully erect nipples. Red lifted his hips, seeking the sweet satisfaction of penetration, but Stretch moved away.

“what the fuck?” growled Red, irritated by the delay.

“do you know what the speed limit of sex is, Red?” asked Stretch with a shit-eating grin.

Red considered punching him as an answer. His nipples ached and his pussy was absolutely begging to be filled.

“it’s 68, because at 69, you have to turn around.” Stretch answered his own question, twirling his finger in a circle to demonstrate.

“i really hate you,” sighed Red, pushing Stretch down on the bed and taking up a position with his pussy tantalizingly close to his boyfriend’s mouth. He thought about biting the throbbing cock twitching in front of his face, but before long, Stretch’s expert tongue-work had Red sloppily sucking his cock and mewling for more.


	18. Day Seventeen: Swapfellcest (Masturbation, Seduction, Collaring, Orgasm Denial)

**Summary for the Chapter:**

> Pairing: SF!Sans x SF!Papyrus (Swapfellcest)
> 
> Featured Kinks: Masturbation, Seduction, Collaring, Orgasm Denial
> 
> Additional Warnings: Fontcest/Swapfellcest, Bondage, Sadism/Masochism

The chains holding him rattled as he struggled against them. Thick dark orange leather dug into the bones of his neck. A low buzzing filled the room from the vibrating cock ring he wore. The restraints held firm, but the reward for breaking them drove Mutt to fight.

His Lord reclined, naked, on a chaise lounge mere feet away from him, tapping a riding crop idly on the palm of one hand. He could see his Lord’s violet magic glowing low in his pelvic inlet; he could smell it too, the arousal potent in the still air. Drool escaped around the bit gag between Mutt’s sharpened teeth. He longed to pounce on his Lord, bend him over the arm of the chaise, and fuck him until he fainted.

Blackberry rose to his feet and strode imperiously over to his brother, who he referred to simply as Mutt. He always forced Mutt to kneel during their sessions because he wanted to tower over his much taller brother. Blackberry stood stood just outside of Mutt’s reach, tantalizingly close, but infuriatingly beyond his grasp.

”PATHETIC,” snapped Blackberry, striking Mutt across the face with his crop. Blood trickled from the gold-fanged skeleton’s mouth. He stared at the ground, accepting his Lord’s punishment. “HOW COULD MY OWN BROTHER ALLOW SUCH FLIMSY BINDINGS TO HOLD HIM?” He nudged one of the heavy chain links with his riding crop, making it jangle.

Mutt remained still which only set Blackberry off more. “YOU DON’T DESERVE THAT COLLAR YOU’RE WEARING.” Blackberry reached for the collar- the handtooled leather that match his brother’s magic color, the gold spikes that protected his brother’s vulnerable neck, the tag bearing his insignia- and Mutt recoiled.

“YOU APPEAR TO VALUE MY OWNERSHIP AFTER ALL, MUTT, SO TELL ME,” Black snarled, “WHY THIS-” Blackberry seated himself on the chaise lounge again, spread his legs, and gestured at his dribbling pussy “- ISN’T WORTH BREAKING THOSE CHAINS FOR?”

Mutt chomped at his bit gag. His Lord had placed him in these bindings, now he was expected to free himself from them? He wore his collar, the collar that his brother had placed around his neck personally, to show his loyalty and obedience to his Lord’s orders. If Black gave permission for him to break the chains, then nothing would hold him back from his goal- his Lord’s silky folds and hot, tight cunt.

Mutt lunged, rearing upright and throwing all of his weight, strength, and determination into his forward movement. The chains held for only a few short seconds before they buckled under the strain of Mutt’s charge. With a PING, the links separated, allowing Mutt free range of motion, which he used to rush to his Lord with single-minded focus.

“SIT,” ordered Blackberry in a cool, commanding tone. Mutt instantly dropped into a crouch at his Lord feet. His Lord’s words bound him in a way that no physical material ever could. Blackberry smirked. Nothing aroused him quite like exerting control over a monster who displayed such raw power.

Blackberry loved the way that Mutt stared at him. He loved that Mutt couldn’t tear his eyes away from the slick slowly leaking from his pussy to stain his thighs. His horny brother kept swallowing every time his drool filled his gagged mouth, and Mutt’s dark orange cock twitched and bobbed as thoughts of fucking his brother in every position imaginable played through his mind. Precum gathered at the tip of his cock to drip on the floor, forming a puddle similar to the one that darkened the carpet where he’d been chained up. Mutt didn’t budge though. His Lord’s orders froze him to spot until they were rescinded or Mutt himself dusted.

The dog deserved a reward, so Black ran one finger up and down his slit between his puffy pussy lips until it glistened with his juices. His bones tingled with even that slight stimulation, and he closed his sockets, relaxing into the pleasure of touching himself in front of his subservient, perfectly controlled brother.

Mutt trembled from the effort of staying in place. He wished it was his phalanges exploring his brother’s soaking cunt, but he would await his orders. In the meantime, he enjoyed the show with undivided attention.

Blackberry splayed the fingers of one hand to hold his folds open and put his pussy on display for his brother. He allowed Mutt to get a good look at his fluttering, greedy hole as he used his thumb to firmly stroke his sensitive clit.

Black moaned, loudly and lewdly, not holding anything back. He slipped a finger inside his tight little hole, but it didn’t satisfy him, so he added another, pumping the digits hard and fast while continuing to play with his clit. Pressure built slowly in his abdomen. His fingers weren’t enough. They were never enough. He needed his brother’s thick, throbbing cock to destroy him and bring him that sweet, euphoric release.

Withdrawing his fingers, Black pointed at Mutt, then at himself. “GET TO WORK, MUTT. NOW.” The last word had barely escaped his throat when Mutt collided with him, grabbing his femurs and forcing them back towards his chest for a better angle.of entry. With a feral growl, Mutt slammed his cock into his Lord’s deliciously tight little cunt.

Mutt loved the sensation of his Lord’s walls clenching around him, but the vibrating cock ring prevented him from cumming, and the need to release his hot load into his Lord became overwhelming. He wanted to cum. He needed to cum. He needed to fill his Lord with his magic until it overflowed his pussy and left him gaping and exhausted for days.

Mutt fumbled with the cock ring without slowing his punishing pace. His rough thrusts rocked his Lord’s small body, but he craved the absolute pleasure of cumming inside of his small but fierce brother.

“LEAVE IT,” commanded Black, gasping for air as he neared orgasm. “YOU’LL CUM WHEN I GIVE YOU PERMISSION TO CUM.” It was going to be a long night, and Black planned to enjoy every moment of it.


	19. Day Eighteen: Kustard (Fucking Machine, Role Reversal)

**Summary for the Chapter:**

> Pairing: UT!Sans x UF!Sans (Kustard)
> 
> Featured Kinks: Fucking Machine, Role Reversal
> 
> Additional Warnings: Bondage

“so what’s the surprise?” asked Red for the umpteenth time since Sans had placed the blindfold over his eyesockets and instructed him to wait. “and why do I gotta be all trussed up for it?”

“i had to tie your hands behind your back because you kept trying to take the blindfold off, remember?” explained Sans patiently, also for the umpteenth time. That was, in fact, only part of the reason for the bindings. Sans took a moment away from setting up his surprise to admire the handiwork on the knots.

Usually Red tied  _him_  up during sex, but today they were switching roles. Sans would be taking charge. Sans would being the one controlling his partner’s pleasure, and that included operating the fucking machine now set up and ready to go in their bedroom. As soon as Sans settled his boyfriend into the proper position, the real fun could begin.

Sans guided Red into a kneeling position and hooked his bound hands to one of the suspension chains that hung from the bedroom ceiling. He adjusted the length of the chain until Red was tipped slightly forward with his pussy open and exposed for the dildo attached to the fucking machine- a faintly glowing blue ecto-cock that Sans had formed from his own magic.

Before removing the blindfold, Sans double-checked the machine, making sure to line up and lube the cock properly for painless entry. Standing over Red, Sans basked in the sense of power he felt with Red immobile and sightless in front of him. Reaching down, he slipped a finger into his boyfriend’s pussy. His finger slid in easily and came out glistening with arousal. Red was ready.

Sans removed the blindfold with a flourish, and Red blinked in surprise at the sight of… the wall of their room. Sans wasn’t even standing in front of him. He might as well still have the blindfold on! Red opened his mouth to make a snarky comment about the so-called surprise when he heard a small engine whirring to life somewhere behind him. What could Sans possibly be doing back there? Red soon found out.

The tip of the dildo pushed past Red’s pussy lips and slowly entered him. Even lubed and with Red’s pussy nice and wet, the size of the dildo meant it dragged against Red’s entrance, fighting its way inside. Sans almost dropped the remote controlling the machine as pleasure jolted through his bones. Fuck, it felt amazing, and the machine was still on a low setting to allow Red to adjust.

“is this a fucking machine?” squawked Red when the dildo withdrew only to pound into him again setting a slow but powerful rhythm that hit all the right spots inside of him. “i didn’t know ya had it in ya.” Red widened his stance slightly, inviting the repeated violations with gusto.

“actually, you’re the one who has it in ya this time, Red,” teased Sans with a smirk. He pointed to the mirrors he’d set up so that Red could see Sans’ ecto-cock slamming into his pussy. While Red was distracted by watching the blue magic pump in and out of him, Sans took the opportunity to crank up the setting.

Red shrieked. His pussy clamped down around the invading dildo as it picked up speed. Sans gasped and panted, rubbing the front of his pelvis. Red’s pussy squeezed him so tightly that he almost couldn’t stand the intensity of it.Red’s tongue lolled out, dripping saliva onto his chin. The thickness of Sans’ cock and the force and pace of the fucking machine filled him up so well that he could barely stand it either, and the settings still went much higher.

Sans turned the device to an even higher setting with trembling hands. The dildo slammed into Red with brutal speed and force, bringing Sans to his knees and making Red scream and tense up until he squirted. Red’s pussy juices flowed over Sans’ detached cock, but the other skeleton barely noticed through the fog of pleasure that enveloped him.

“so close…” moaned Sans on his hands and knees. “almost… ah… AAAHH!”

Sans body spasmed, and he came hard. The fucking machine never stopped its merciless thrusting as cum spilled out of Sans’ cock and into Red’s battered pussy. The device continued pounding away at Red, unwavering and indifferent to the orgasms, and cum bubbled out of Red’s throbbing hole with every movement to drip down onto the carpet.

The machine finally stilled. Sans pressed the OFF button and dismissed his magic. He crawled over to Red, still too wobbly from the violent orgasm to actually stand up. Sans unhooked and untied Red’s hands, and those hands and arms found their way around his body.

The pair of skeletons curled up on the floor, savoring the afterglow together. Sans rested his cheekbone on Red’s ribcage, sockets drooping with exhaustion. Right before he lost consciousness, he heard Red whisper to him:

“we should switch roles more often.”


	20. Day Nineteen: UL!Sans x Reader (Public, Formal Wear, Cock-Warming)

**Summary for the Chapter:**

> Pairing: UL!Sans x Reader
> 
> Featured Kinks: Public, Formal Wear, Cock-Warming
> 
> Additional Warnings: Gender Neutral Reader

You noticed him from across the room; it would’ve been impossible not to. The tuxedo-clad skeleton wore his charisma like a fine perfume, and you followed it like a bloodhound on the scent. He knew you were watching him. You saw him glance at you from time to time as you worked your way around the room to meet him. He simply waited, letting you come to him.

What prompted the strong attraction you felt towards the handsome skeleton. Was it his heart-shaped eyelights? His smooth, sultry voice? The spattering of freckles lit up by the faint purple blush on his cheekbones? Maybe he exuded some sort sort of pheromone that your body found irresistible. Regardless of the reason, when he asked you if you wanted to have a good time, you breathed a soft “yes.”

Smiling a cocky smile, the skeleton caressed your cheek with one hand. You leaned into his touch, and he whispered instructions softly into your ear:

“Go to the coat closet and wait for me.”

You nodded, distracted, and floated to the agreed-upon destination on clouds of tantalizing desire. You slipped into the coat closet. There was no lock on the door. Anyone could walk in at any time and catch the two of you messing around. The thrill of possible discovery made your heart race, and your skeleton suitor hadn’t even arrived yet.

The door opened slowly, and you instinctively shrank back into the shadows in an attempt to hide yourself from prying eyes. The eyes that entered the small space were the kind whose prying you welcomed, though. The sexy skeleton with the suave flair smiled that provocative smile at you again, and any reservations you might have had about closet sex at a crowded party melted away.

“You look absolutely mesmerizing in formal wear, love, but I bet you look even better out of it,” the skeleton purred, prowling closer to you without touching you as if he wanted to gauge your reaction before making a move. “They call me Lust… with good reason,” he said with a wink.

“You can call me yours,” you replied, playing his flirtatious game. You beckoned him forward with one curling finger, inviting him to show off the reason for his moniker, and he obliged eagerly.

Loosening his tie, Lust stepped forward until his hips brushed yours. His hands infiltrated your clothing like skin-seeking missiles, but his touches were teasing and gentle, not demanding. While his hands explored your undergarments, his mouth found your neck, planting chaste kisses along your jawline and breathing warm, soft breaths against the sensitive skin behind your ear. Every touch, every kiss was electrifying.

Lust’s teeth caught your earlobe, nipping and tugging at it before releasing it to travel to your mouth for a deep, knee-weakening kiss. You moaned and  swooned against him, but his strong arms surrounded you and held you upright despite the fact that his hands were dipping down into your underwear.

You didn’t protest or stop him when he turned you to face the wall. You braced your hands on the faux wood paneling to steady yourself, and Lust tugged down your underwear, making you gasp. Kissing the back of your neck and growling amorously, Lust slipped a finger into your entrance, pumping gently to stretch you out. You spread your legs wider to accommodate him, and he chuckled. The sound vibrated through your body, sending shivers racing up and down your spine.

Lust added another finger. He took his time, scissoring his fingers and working them in and out steadily until you were begging him for something bigger, something thicker. You wanted his cock, not his fingers. You could finger yourself at home. Your eyes widened in surprise when his heavy, warm length slapped your asscheek.

Were you really about to have a random party hook-up in a coat closet with a skeleton monster that you just met? The sensation of Lust rubbing the head of his cock against your entrance answered that question for you with a resounding “yes.”

Lust lived up to his name, filling you up with his huge cock and destroying your tight hole in the best possible way. He manipulated your limbs, switching from one position to another for maximum thrust and penetration, and he slammed into your tight hole at a furious pace no matter what position you were in. His hips snapped powerfully, his hands continued to caress your body, and his voice kept murmuring for you to remain silent at the risk of being discovered.

You lost count of the small orgasms, the ones that caused a tingle and spasm but faded quickly. The way Lust’s fingers dug into your flesh with wild abandon told you that he was close to his own orgasm, and you felt a more intense pressure gathering low in your abdomen. You wouldn’t be able to stop yourself from screaming when it finally released.

You covered your mouth to stifle the sound but second before the orgasm hit, you heard the doorknob to the coat closet rattling. Voices became audible as the door creaked open.

“Lust… someone’s coming,” you mewled desperately… desperately because someone was cumming, two someones actually. Lust shot his load deep inside of you at the same time that your walls clenched, your body tensed, and pleasure engulfed you, followed quickly by panic.

Whoever was in the room could see you. They would know exactly what you were doing, exactly what you’d just finished doing. Hysteria fought bliss until you realized that you weren’t pressed against the wall of a coat closet. You were laying in a very plush and comfortable bed.

“Wha…?” you mumbled, a bit dazed and confused by the mix of conflicting emotions and change of scenery.

“I teleported us away, love. Nobody saw anything,” Lust reassured you. He kissed the top of your head, and you relaxed into his arms. He didn’t pull out. Instead, you fell asleep in his arms with his cock, still semi-hard, buried inside of you, and honestly, it didn’t bother you in the slightest.


	21. Day Twenty: MapleBlossom (Hot-Dogging, Dirty Talk)

**Summary for the Chapter:**

> Pairing: UT!Papyrus x SF!Papyrus (MapleBlossom), Classic fontcest (implied), Swapfellcest (implied)
> 
> Featured Kinks: Hot-Dogging, Dirty Talk
> 
> Additional Warnings: Fontcest/Swapfellcest. Voyeurism, Bondage and Dominance

“Thank You For The Assistance, Blackberry,” Papyrus said when the fearsome Swapfell Sans opened the door and waved him into his luxuriously appointed home. This Papyrus was always so polite and soft-spoken, two characteristics that Black intended to cure him of during today’s lesson in domination.

“Blue Informed Me Of Your Particular Needs, And I Must Say, You’ve Come To The Right Place.” Black led Papyrus down the stairs and into the basement. The smaller skeleton flipped a light switch to reveal his own Papyrus, stripped naked and bent over a breeding block. The wrist and ankle shackles weren’t attached, yet Mutt, as the Swapfell Papyrus was known, did not move or even blink as his Lord and his Lord’s guest circled him.

“My Brother Does Not Treat Me Like A Mature Adult. Does He Truly Think I Have Never Fantasized Or Watched Pornography On The Undernet? That I’ve Never Masturbated? I Want Him To Respect Me, And I Want To Dominate Him During Sex The Way That Blue Does With His Brother.,” Papyrus grumbled.

“Blue Learned Everything He Knows From Me,” boasted Blackberry, “And I’ll Teach You All Of The Same Techniques.” Black lifted Mutt’s chin, forcing his brother to meet his eyelights. “You’ll Be Practicing On Mutt Here. Summon Your Ecto, Mutt.”

“yes, M’Lord,” Mutt rumbled in his gruff drawl. Dark orange magic swirled and formed into a lean ecto-body complete with a firm, toned ass, and a delicate pussy.

Black didn’t bother checking Mutt’s obedience; he knew his brother would do as he ordered. The short but imperious skeleton strode over to a wall where manacles, leashes, and silk ropes hung in neat rows. He selected a leather leash that matched the collar around Mutt’s neck and handed it to Papyrus.

“A Collar And Leash Establish The Dynamic Of Power In A Relationship,” explained Blackberry. “I Recommend That You Get A Set For Your Own Brother.”

Papyrus nodded, then he stepped forward and hesitantly clipped the leash to the ring in Mutt’s collar. Mutt smirked at him, showing off a gleaming gold fang. Papyrus faltered in the face of Mutt’s flippant disrespect. Suddenly, doubts clouded his mind. What if Sans refused to wear the collar? Blackberry saw his new pupil rapidly wilting.

“Do Not Allow Him To Disrespect You. Put Him In His Place,” Blackberry barked at Papyrus. Mutt never dared to smirk at his Lord unless he wanted a punishment, but clearly he intended to test Papyrus early on in the lesson.

Papyrus closed his sockets and inhaled deeply. He envisioned his brother bent over in front of him. He imagined affixing a collar and leash to Sans’ neck, then pictured Sans giving him that same patronizing look, a look that clearly said his brother didn’t take him seriously and refused to acknowledge his control.

When Papyrus’ sockets opened once more, his eyelights flashed with determination. Papyrus yanked the leash upwards savagely, forcing Mutt’s neck into an uncomfortable angle and holding it there. Locking eyelights with the collared skeleton, Papyrus proceeded to grind his clothed erection into Mutt’s face.

“If You Insist On Making Such Belligerent Expressions, I Will Be Forced To Put Your Mouth To Better Use. It Is Difficult To Disrespect Someone When You’re Choking On Their Cock…” Papyrus let his threat sink in, then tilted his hips and dragged his cock across Mutt’s eye socket, letting the straining outline of the head of his cock, still encapsulated in his hot pants, catch on the rim of the socket. “… Or Worse.”

Mutt’s pussy convulsed at the idea of such uncharacteristic roughness from the usually gentle skeleton. The masochist loved a good punishment, especially when it involved pain and sex. Blackberry nodded approvingly from his vantage point across the room. Papyrus certainly possessed a great deal of hidden potential.  _Who would have ever guessed it?_

“Don’t Fuck Him Yet. Make Him Beg You For It,” suggested Blackberry. Withholding sexual pleasure often proved to be an effective way to make an obstinate partner submit.

Papyrus grunted in agreement, still focused on Mutt, superimposed with an image of his own brother. Yes, he wanted Sans to beg. He wanted Sans to squirm, to cry, to plead, and finally, to yield to his brother’s dominance. Still holding the leash, he stepped around the breeding block until he stood behind Mutt.

Papyrus’ gaze swept over Mutt, taking in the curve of his ass and his trembling pussy. Using two fingers, Papyrus spread Mutt’s pussy lips open, allowing arousal to dribble out of Mutt’s pulsating cunt onto his hand. He brushed Mutt’s clit lightly with a single phalange, making the other skeleton jolt as intense pleasure shot through his body. Papyrus chuckled as he withdrew his hand. There would be time for orgasms later… when  _he_  decided to give them.

Mutt whimpered at the sudden absence of touch, but he didn’t have to wait long for Papyrus’ hands to return. This time Papyrus grabbed his asscheeks, sinking his phalanges in and kneading the ecto-flesh of Mutt’s ass. As he had done with Mutt’s pussy, Papyrus spread Mutt’s asscheeks apart, revealing a tightly puckered entrance. Papyrus wasn’t interested in anal sex though, not yet anyway.

Removing and neatly folding his hot pants before placing them carefully on the floor, Papyrus grabbed a handful of his skin tight bodysuit and tore the thin fabric, letting his cock bob free. Stroking it a few times, Papyrus settled the thick shaft between Mutt’s asscheeks, and then pushed the firm, smooth ecto-flesh together until it squeezed his cock like a fleshlight.

Throwing back his head, Papyrus groaned as he rutted powerfully against Mutt’s ass without entering him. Mutt wriggled and writhed, seeking the sweet satisfaction of penetration, but Papyrus held back. It was time to make Mutt beg.

“You Like This Don’t You? You Like The Feel of My Thick Cock,” Papyrus continued to thrust powerfully, cock sliding along Mutt’s ass crack, tantalizingly close to his ass and pussy holes.

“yes,” whimpered Mutt.

“Say It,” snapped Papyrus.

“i love your thick cock… please…”

“Please What?” The movement of Papyrus’ hips slowed, and Mutt panicked at the loss of stimulation.

“please… please fuck me… no more teasing please… i need it… i need your cock inside of me,” Mutt begged. Mutt wiggled his ass enticingly, and Papyrus could see that his pussy was soaked and dripping arousal onto his thighs.

“Tell Me Exactly What You Want. I Want To Hear You Say It. Convince Me That You Deserve My Attention.” Papyrus stepped back, leaving his hand resting on Mutt’s hip.

“fuck my slutty cunt with your cock. use me like a cocksleeve. fill every one of my filthy holes with your cum. make me your whore, just please fuck me… destroy me,” Mutt babbled, nearly delirious with sexual tension.

“I Don’t Know If You Really Deserve It,” Papyrus said with a wicked smile.

 _Well, well, well,_  thought Blackberry,  _Papyrus was turning out to be a star pupil._ By the time he showed mercy to poor Mutt, the Swapfell Papyrus had become a perfect little submissive for him… in just one session.


	22. Day Twenty-One: Error x UL!Sans (Bukkake, Suspension)

**Summary for the Chapter:**

> Pairing: Error x UL!Sans 
> 
> Featured Kinks: Bukkake, Suspension
> 
> Additional Warnings: Voyeurism, Sex Work/Prostitution

Error perused the ever increasing number of alternate universe and divergent timelines in the Doodle Sphere with a scowl on his face. Ink was nowhere to be seen, and Error seized the chance to find one of these disgusting abominations, these glitches, and destroy it. Which one would it be?

The skeleton peered through a portal. The surroundings were dark, and the scent of blood hung thick in the air. Unseen creatures snarled and stalked through the darkness. Error decided to leave that particular universe for Ink. Hopefully it would give the paint brush wielding freak nightmares…

After checking several more gates that held nothing of interest to him, Error finally discovered a perfect universe to destroy. It contained everything he hated- bright colors, open sexuality, and major variations from the core timeline. Something stopped him from wiping it out instantly though. For some reason, he wanted to explore this strange universe of Underlust first.

What was the worst that could happen?

None of the monsters he passed in the streets of Snowdin spared him so much as a second glance. Apparently cross-timeline visitors were common around here. All the more reason to destroy this irritating anomaly to prevent it from causing further glitches in the multiverse like an unstoppable plague. Nothing disgusted Error more than crossover universes and mixed timelines.

Scowl deepening, Error arrived at the Grillby’s in Underlust only to discover that instead of a bar and restaurant, the establishment appeared to be some sort of strip club or sex dungeon. The first floor was crowded with handsy patrons, so Error quickly made his way down a flight of stairs into a private viewing area. Ugh. To think that those sweaty perverts had nearly touched him…  _Unacceptable!_

Error seethed with rage that hid his secret phobia of being touched. Physical touch made his bones crawl, and prolonged contact or unexpected touches felt like burns that lasted for hours. Yes, this universe must be destroyed as soon as possible, but first, his curiosity needed to be sated. Maybe he would just take a quick peek through one of the two-way windows that lined the room.

Reminding himself that the room’s occupants couldn’t see him, Error stepped up to the first pane of glass. A naked skeleton with a purple ecto-body laid on an opulent bed that looked like something out of a fairy tale. The other monsters crowded around could hardly be considering Prince Charmings administering true love’s first kiss though. Each monster had his cock in his hands or paws, and they were all pumping away frantically.

The skeleton that reclined on the bed touched his pussy with one hand and circled the protruding nipple on one of his ample breasts with the other. He panted freely, allowing his tongue to hang out of his mouth with saliva dripping from it. Despite the debauchery, the skeleton seemed to be enjoying himself.

Though the well insulated walls of the room absorbed the noises that the prone skeleton made, Error could tell he was screaming “yes” the moment thick, sticky ropes of cum started raining down all over his face and body. Monster after monster came and spilled their load onto pale ivory bones or smooth purple ecto-flesh. The skeleton monster posed with his index and middle fingers up in a V-shape with both hands once all of the monsters had finished painting him with their cum.

While the other monsters were busy admiring their handiwork, the purple-magicked Underlust skeleton rubbed his hands in the cum coating his body. Lifting his hands to his face, he licked the mess off of his palms, eyelights half-lidded in bliss. Error found himself staring at the skeleton monster long after the customers had crept away. The skeleton, and the activities he engaged in, captivated Error.

The destroyer of universes lingered in the strip club basement even after the other skeleton disappeared from the private room. He jumped in surprise when a low voice purred close to his skull. He was so lost in his private fantasies that he hadn’t even heard the other monster approaching.

“see something you like?” asked the skeleton from the bukkake session with a seductive smile. The cum had been cleaned away, and the skeleton had a bathrobe pulled snugly around his body. The skeleton swept Error’s body with his heart-shaped eyelights. “i don’t have any customers for another hour or so if you want to have some fun.”

Error hissed and scrambled away from the Underlust skeleton. “Don’t touch me!” he screeched, throwing loops of his blue strings around Lust’s wrists and ankles and yanking him off of his feet to swing, suspended, well outside of touching distance. In the flurry of movement, Lust’s bathrobe fell open, exposing his breasts and the smooth mound of his pussy.

Error stared despite his best efforts not to. He couldn’t pull his eyelights away from that lithe body and the memory of how it had been used. Manipulating the strings that held Lust, Error adjusted his body into the same position he’d laid in on the bed- body horizontal and legs spread.

“i don’t mind if you do the touching,” chuckled Lust. “if the control makes you more comfortable, then i’m your little sex toy for the evening… this time.” Lust winked.

Error’s strings prevented Lust from lifting so much as a finger without his say-so. Suspended in midair, Lust could not get any leverage to break free or even move on his own. He was completely helpless and at Error’s mercy with no risk at all of him touching the severely haphephobic skeleton.

Error licked his teeth thoughtfully with his multiple tongues. It couldn’t hurt to have a taste of that delectable pussy, could it?

Error spent the first part of his allotted hour tongue-fucking Lust and drinking his juices down like sweet nectar, followed by an intense session of fucking Lust’s mouth and pussy with his cock until the captive skeleton screamed and squirted and begged him for more. By the time Error popped back back out of the Underlust universe, Lust was a sloppy, whimpering mess of drool and cum on Grillby’s basement floor.

Looking back over his shoulder at the shimmering portal to Underlust, Error decided that he would let this particular universe continue to exist… and possibly return to it again soon.


	23. Day Twenty-Two: PapayaBerry+ (Cuckolding, Handjobs, Threesome (or more)

**Summary for the Chapter:**

> Pairing: UT!Papyrus x US!Sans x UT!Sans x US!Papyrus (PapayaBerry, StonerBros, HoneyKetchup, Classic Fontcest, Swapcest)
> 
> Featured Kinks: Cuckolding, Handjobs, Threesome (or more)
> 
> Additional Warnings: Fontcest/Swapcest, Voyeurism, Blowjob, Outdoors

“hey, Sans, you haven’t seen Blue around have you?” asked Stretch, appearing out of nowhere in the middle of his friend’s living room with a  _POP_  of displaced air.

“yeah, he’s out training with my bro in the woods,” replied Sans, not at all surprised to see Stretch teleporting directly into his home. Since the Underswaps had discovered the Undertale universe, the skeleton brothers became frequent visitors to each other’s homes, and lazybones like Stretch and Sans never arrived by such mundane means as walking.

“again?” Recently, Blue and Papyrus had been spending more and more time together. Stretch wondered if Blue was trying to replace him with a more energetic and like-minded model. They barely spent any time together nowadays. “he’s been coming here every day for the last week. he’s even missing his training sessions with our Alphys, and he never shirks his Royal Guard-in-Training duties!”

Slowly, Sans sat upright on the sofa. Normally nonchalant in every situation, Stretch’s words actually gave Sans cause for concern. Undyne had called last night to ask why Papyrus hadn’t stopped by her house for training that day, and Sans had brushed it off. Maybe his bro just needed a break. Now he wasn’t so sure. “do you think something’s going on with them?”

“i don’t know,” admitted Stretch, “but i think we should find out.”

Papyrus and Blue weren’t usually difficult to locate. Even the vast expanse of Snowdin Forest couldn’t contain the two energetic skeletons’ exuberant voices. Today, however, not a single “nyeh” or “mweh” hung in the still crisp air or echoed between the cliffs. Fortunately for Stretch and Sans, their brothers’ boots still left two convenient sets of tracks in the ever-present snow which the two hoodie-clad skeletons easily followed.

Sans imagined that he and Stretch would be out all day checking each of Papyrus’ usual hangouts- the sentry stations, the cliff where he once painted an elaborate rope bridge facade, or one of the many sites of the puzzles that he’d set up in case a human ever showed up in the Underground. Maybe their brothers weren’t even in Snowdin; maybe they’d gone elsewhere for their battle training. Much to his surprise, Blue and Papyrus hadn’t gotten far… and they weren’t trading battle techniques either.

Muffled noises nearby alerted the Underswap skeleton to their brothers’ presences while Sans was still lost in thought. Stretch’s outstretched arm stopped Sans in his tracks. Holding up one phalange to his mouth for silence, the taller skeleton gestured for his companion to look into a small clearing just off of the trail. Sans peeked around a bush and saw the source of the sounds.

Blue leaned against a tree with one gloved hand covering his mouth to stifle the whimpers and moans coming from it. The other hand rested on Papyrus’ skull. Papyrus knelt in the snow, with his face level with Blue’s pelvis. Blue’s pants were down. Papyrus clung to Blue’s hipbones as his head moved rapidly back and forth… around a blue glow… while making slurping sounds…

It finally dawned on Sans what their brothers were doing. Clenching both his teeth and his fists, he prepared to stomp into the clearing and give Blue a piece of his mind, but Stretch grabbed his arm before he had a chance to act.

“just watch,” mouthed Stretch.

Sans’ magic seethed inside of him, but he allowed Stretch to hold him back. What would he even say to his brother anyway? That it should be his cock thrusting into his brother’s throat? That it should be his eyelights rolling back in his skull from pleasure? His fingertips scraping his brother’s skull as that orange tongue went to work? Fuck, he wanted so badly to feel his brother sucking and swallowing around his cock, but it wasn’t him. It was Blue.

Saliva coated Blue’s cock, and it dripped down into the snow each time Papyrus’ head moved far enough back for Sans to see it. The wetness and suction combined to make a squelching noise that seemed so loud in the surrounding silence. Blue bit down on his hand to keep from crying out. His bucking hips stuttered.

Sans didn’t know why he kept watching. Blue snapped his hips forward and pulled Papyrus’ skull to meet them, sinking his cock as far down Papyrus’ throat as it would go before he came. Both skeletons closed their sockets, and Sans could see excess cum dripping out of his brother’s mouth as he fought to swallow all of it.

“Oh, Stars, Sans,” murmured Papyrus, licking a stray strand of cum from the corner of his mouth. Sans froze.

“i thought Papyrus called your brother ‘Blue,’” Sans whispered to Stretch, who still stared intently at their brothers.

“So Good… Papy,” mewled Blue.

“i’m the only one he refers to as Papy,” Stretch murmured more to himself than to Sans.

Blue and Papyrus kissed sloppily, hands fondling each other’s ribcages in a frenzy of lust. Occasional moans of “Sans” or “Papy” could be heard between the gasps and moans as their hands moved lower. Blue palmed his cock and with a few pumps, it became fully erect again. Papyrus slid his shorts down, revealing a bright orange pussy nestled in his pelvic inlet, glistening with arousal and ready to be fucked.

Magic swirled low in Sans’ own pelvis. Suddenly Stretch’s hands were there, stroking his pubic symphysis as a thick blue cock formed from Sans’ sexually-charged magic. Stretch squeezed and stroked his friend’s shaft, rubbing the tip with his thumb to coax out some precum to lubricate it. Sans leaned back into the Underswap skeleton’s chest. He could see how easy it would be to imagine a skeleton from a similar universe as one’s own brother.

Stretch squeezed his cock harder, running his hand from the base of the shorter skeleton’s cock all the way to the tip slowly, but with growing fervor and speed. Sans struggled to stay quiet. How embarrassing would it be to be caught spying on his brother and his brother’s lover with his pants down while his brother’s lookalike gave him a handjob in the bushes?

“st-stop,” hissed Sans, and Stretch immediately removed his hand, apologizing.

“i just thought that since they were messing around while thinking of us, maybe we should do the same-” Sans cut of Stretch’s explanation.

“-or we could join them,” he suggested mischievously to the other skeleton.

Sans and Stretch stepped into the clearing, startling Blue and Papyrus. After some hasty explanations, all four skeletons decided to set aside their issues with the situation for the moment in favor of some naughty outdoor foursome fun.

Two nearly identical short skeletons held their brothers pressed together, chest to chest, hands clasping to steady themselves. The taller set of not-quite-twins kissed, tongues probing and stroking each other. The shorter brothers rubbed their throbbing cocks on soaking orange pussies, slick enough with arousal to allow them easy entry.

Cries of Papy, Sans, Sansy, and Paps intermingled long into the night until it became impossible to tell who was screaming for whom.


	24. Day Twenty-Three: Kustard (Scars, Master/Slave, Shibari, Size Difference)

**Summary for the Chapter:**

> Pairing: UF!Sans x Bara UT!Sans
> 
> Featured Kinks: Scars, Master/Slave, Shibari, Size Difference
> 
> Additional Warnings: Self-Harm (Mention)

_How could the same skeleton from a different universe be so vastly different in size,_  wondered Red, staring up at his very large boyfriend and owner. To be honest, he actually enjoyed being the small one here in the safety of their home. Those giant arms around him made him feel safe and protected in a way that he never did in Underfell.

Red didn’t dwell on unanswerable questions though. Instead, he stood perfectly still while Sans’ large but gentle hands carefully stripped him of his clothing.

Sans never rushed when removing Red’s clothes. He liked to caress his boyfriend (and slave)’s bones lovingly, one by one, checking them to make sure they had healed properly from Red’s former life of hardship. He also surreptitiously checked for any new injuries- a sign that Red might be struggling emotionally.

Since Red had sworn himself to servitude to the huge Sans for saving his life and bringing him to a peaceful timeline to live, Sans had taken his position as Master very seriously. Red belonged to him, and though the big skeleton rarely conducted routine maintenance on any of his possessions (that’s what he had a servant for, after all), he treasured Red and ensured that Red received the utmost hands-on care, including daily inspections.

“speak,” ordered Sans once he satisfied himself that Red’s emotions hadn’t overwhelmed him into harming himself. He was lazy, sure, but he was also eerily observant. It might have had something to do with the way Red kept rubbing at his sternum and averting his eyelights whenever Sans touched one of his many, many scars.

“the nightmares started again,” reported Red.

“we have ways of dealing with that though, don’t we,” rumbled the big bara skeleton, padding- very lightly for his size- over to the bedroom closet.

“yes, Master,” murmured Red, standing as still as he could despite the shivers of anticipation coursing through his body. When his thoughts, conscious or subconscious, spun out of control, his master took that control and responsibility away from him, usually through intense sexual experiences. Master definitely treated him well.

Sans loved the way that Red called him Master. Such a small and submissive partner suited him well. The big skeleton opened the closet door and perused its contents with Red’s specific needs in mind. He wanted to do Red’s reverence justice by selecting just the right toys for today’s session.

The closet contained a variety of implements and devices lining the shelves and hanging from pegs. Sans ignored the sensory deprivation equipment; Red shouldn’t be left alone with thoughts of his recurring nightmares. Sans also bypassed a variety of dildos, anal plugs, and sounding rods. Today, Red needed to be touched to remind him of the reality he currently lived in. Finally, Sans’ eyelights found the perfect item- silk ropes.

Shibari would be relaxing for Red, and it allowed Sans to put his hands all over his little slave’s body. The tight knots would render Red motionless and helpless, reminding him of who he truly belonged to. Sans grabbed the ropes from the closet, and instructed Red to sit on the bed. Red stared at the ropes with greedy eyelights as he obeyed.

Sans began the intricate rope-tying ritual by binding Red’s forearms together behind his back with his hands each holding the elbow of the opposite arm. Sans then moved on to Red’s legs, securing the smaller skeleton’s femurs to his lower legs then seating him on them. Now that Red was bound and in position, Sans could begin the artistic and intricate knot-tying of shibari.

Red’s sockets closed, and the tension eased from his body. Sans laid the soft silk ropes over his shoulders, tying the ends around Red’s ankles to anchor them. Slowly, gently, Sans tied knot in the ropes, creating a pattern with one pair of ropes straight down Red’s sternum to his pubic symphysis and the other pairs woven in and out of Red’s ribs before being knotted either with each other or with the central pair of ropes.

Sans used the spaces between the ropes to showcase Red’s scars, not to humiliate him or make him feel weak, but to showcase the beauty of the ivory bones despite what they had endured. By the time Sans finished with Red’s sensitive ribs, the smaller skeleton had summoned his cherry red ecto-body for further attention which Sans gladly gave.

The silk ropes formed a diamond pattern over Red’s stomach, and all of the ropes came together to drape in a fan pattern over Red’s manifested pussy. Sans gathered the ropes together in one hand, tugged them tight against Red’s slit and secured them to Red’s arms before standing back to admire his handiwork.

Red looked gorgeous and vulnerable laying trussed up on the bed, a combination that made Sans’ mouth water. Soon, he told himself. Sans slid a finger between the taut ropes and Red’s pussy, feeling how warm and slick it had gotten in just a few short minutes. Red squirmed, but the ropes held him in position perfectly.

“who do you belong to?” growled Sans. A primal hunger stirred in him, but he needed to do this before he sank his thick cock into that delectable tight little cunt.

“you, Master,” Red responded promptly.

“and who commands your every breath?” Sans tugged on the ropes so that they rubbed against Red’s already-aching pussy.

“only you, Master,” Red gasped. Arousal leaked visibly from his fluttering hole onto Sans’ hand.

“then put aside the nightmares of your past and give yourself to me completely,” demanded Sans.

“yes, Master,” whimpered Red. Master would take care of him. Master would keep him safe and give him pleasure. All he needed to do was submit. The small skeleton went limp with relief, but he jerked back to tension when one of Sans’ huge thick fingers slid into his pussy.

Sans fingered Red roughly with one hand, using the other hand to tug off his shorts. His cock sprang free, already dripping precum onto the blankets. Red would have to wash them tomorrow…  _after_  Sans was done making a thorough mess of both the blankets and his slave.


	25. Day Twenty-Four: RottenBerry (Lapdances, Shower/Bath)

**Summary for the Chapter:**

> Pairing: US!Sans x SF!Sans (RottenBerry)
> 
> Featured Kinks: Lapdances, Shower/Bath
> 
> Additional Warnings: Public Sex

The Magnificent Sanses from Underswap and Swapfell breathed heavily, making their way to the gym locker room after a grueling all-day workout. Blue suspected that he had both surprised and impressed his Fellverse counterpart with his speed and stamina. He admired Blackberry, and his edgier twin’s approval meant a lot to him. They chit-chatted about the highlights of the day’s training while they gathered up towels and a change of clothes from their lockers.

The changing rooms and showers were empty at this time of night. The two skeleton monsters had the benches and the showers to themselves, yet they still chose to strip off their sweat-soaked clothing side-by-side, exchanging surreptitious glances of admiration at each other’s bodies whenever they thought their counterpart wasn’t looking.

Blackberry never expected Blue to have such defined muscle mass, and the skeleton who he had once viewed as soft and weak suddenly possessed a very real sexual appeal to him. When Blue rose from the wooden bench to turn on the hot water in the showers, Black reached out and touched his hand, stopping him.

Blue looked from their hands to Black’s scarred face, bone brow furrowed in silent question. Against his usually indomitable will, Black felt himself flushing hotly under Blue’s intense gaze. An answering blue blush spread across Blue’s cheekbones. At least the attraction was mutual. Black would have hated embarrassing himself with an unrequited crush.

Gauging Black’s reaction as positive, Blue backed up, bending over to grind his ass against the other skeleton’s flaccid cock. Black’s shaft immediately hardened from the stimulation, but Blue didn’t stop. Black’s arms snaked around Blue’s waist to stroke his light blue magic to hardness as well.

Blue spun around, straddling Black’s lap and facing him. Their cocks gently collided, and precum dripped from both tips to mingle at the contact point. Blue resumed gyrating his hips, rubbing their throbbing cocks together, mixing their precum further until both shafts were glistening with it. Black grabbed a double handful of Blue’s ass and pulled him closer, capturing his mouth with an aggressive kiss full of teeth and tongues.

When the two skeleton monsters finally broke apart, they were panting again, though this time it had nothing to do with exercise. Sexual tension crackled in the scant air between their heaving chests.

“Fuck In The Shower?” suggested Black.

“Fuck In The Shower,” agreed Blue, slipping free from Black’s grasp and cranking two of the shower handles to full heat and full flow. The locker room filled with steam in a matter of minutes from the deluge of scalding hot water hitting the cool tiles.

The pale blue glow of Blue’s ecto-body shone like a beacon in the mist, and Black followed it like a moth drawn to a flame. His talus bones clacked on the shower tiles, giving away his position far more effectively than his darker purple magic did.

Black imagined himself to be an apex predator, stalking his unwary prey through the steam, but the tables soon turned when two strong arms shot out of the surrounding fog to ensnare him.  _A trap!_  Blackberry fought down his battle hardened reflexes, and Blue took advantage of his hesitation to push him up against the wall.

Hot water poured down onto Blackberry’s skull and back; the stream of water actually felt good though Black didn’t particularly care for being pinned against a wall. Growling under his breath, Black shoved backwards, but Blue held him firmly. One of Blue’s legs slipped between Black’s, forcing them apart. Was Blue planning to fuck  _him_?

Blue’s cock, warm and slick from the shower, slid between Black’s spread legs. Normally the scarred skeleton would never allow another monster to dominate him, but something about the sensation of Blue’s thick cock rutting on his ass had him arching his back and tilting his hips for more.

A deep chuckle vibrated through Blue’s body when he felt Black responding to his insistent touches. The hot water made foreplay practically unnecessary; Blue explored Black’s tight asshole with two fingers just to check and found it already relaxed enough to take his full length.  _Black must do a different kind of training in the privacy of his own home,_  mused Blue.

The tip of Blue’s cock entered Black’s asshole with minimal effort, and Blue carefully eased the remainder of the thick shaft into Black to prevent any injury.

“Stop Being So Fucking Gentle,” snapped Blackberry. He didn’t want slow, steady thrusts; he wanted a rough, hard pounding that would destroy his tight little hole and leave him screaming for more. Blue happily obliged.

With each powerful snap of his hips, Blue sank into Black’s asshole to his balls, pulling out almost completely before slamming in again with vicious force and speed. He hilted again and again, one hand over Black’s splayed out on the wall, entwining their fingers, the other hand reaching around Black’s waist to jerk him off while Blue fucked him.

The streams of hot water from the showerheads continued to cascade down onto the two skeletons, and everywhere that their smooth ecto-bodies touched their slick and slippery magic slid sensually together.  The skeletons breathed in the steam on ragged breaths, and the pitter-patter of water droplets accentuated the wet slapping of their joining. Black finally gave in to Blue’s dominance and allowed desperate moans to escape his mouth that echoed off of the surrounding tiles.

This facility boasted a state-of-the-art water heater that guaranteed an endless supply of piping hot water to the locker rooms. Blue and Black put that guarantee to the test as they took turns fucking each senseless under the torrid deluge.


	26. Day Twenty-Five: Soriel (Tickling, Olfactophilia)

**Summary for the Chapter:**

> Pairing: UT!Sans x UT!Toriel (Soriel)
> 
> Featured Kinks: Tickling, Olfactophilia (Scent)
> 
> Additional Warnings: Pillow-Humping

Toriel’s side of the bed was still warm; she must have just gotten up. With a contented sigh, Sans rolled over into her spot, absorbing her leftover body heat and inhaling her scent from the pillow. She smelled amazing- like milk and softness and comfort all rolled into one soothing, alluring scent.

Sans pulled her pillow close; he couldn’t get enough of her even when she wasn’t there. Without even opening his sockets, he rocked his hips, slowly humping at her pillow while he sniffed it. Her lingering presence and her intoxicatingly delicious aroma drove him wild and awoke a passionate desire in him that he’d never experienced with anyone else before.

A melodic chuckle interrupted Sans mid-hump. The skeleton monster cracked one eye socket open to see Toriel standing in the doorway, a hand covering her mouth just a moment too late. Sans didn’t bother hiding his activity or the glowing blue bulge in the boxers he slept in. Instead, he crooked a saucy bone eyebrow at her.

“i’ve got a  _bone_  to pick with you, Tori,” said Sans, rolling onto his back and swiveling his hips suggestively. “come back to bed so we can  _work it out_.”

“You shouldn’t say such lewd things in front of a little old lady, Sans,” chastised Toriel through her laughter.

“little old lady? where?” Sans feigned confusion. “i only see a very voluptuous monster who is about to get back in bed with her sexy skeleton lover.”

“Sexy skeleton lover? Where?” Toriel perfectly mimicked Sans’ bewildered expression. “I only see you in our bed dry-humping my pillow.”

Despite her flippant answer, Toriel crawled back into the bed, and Sans scooted over to make room for her. The former Queen didn’t look anywhere near her age in the lacy negligee she wore, and Sans’ hands itched to caress her soft white fur. Toriel was well aware of Sans’ dislike for any sort of physical activity, so she straddled him, taking command of the situation just the way her admittedly sexy skeleton lover preferred.

Toriel had just put a quiche in the oven to bake for brunch, though, so she couldn’t indulge in late morning sex antics with the horny skeleton monster beneath her. Instead, she decided to please Sans in a very different way. Holding up her hands, she wiggled her fingers at him with a mischievous look on her lovely features.

The skeleton’s too-wide grin widened. Toriel knew him so well. She appreciated his humor. She fed him delicious food whenever he wanted it… and she was well-acquainted with every single ticklish bone in his body. She also understood his love of being tickled. Something about the tingle like an electric current through his magic and the lack of control when he began to laugh made tickling a favorite type of play for Sans.

Toriel started by running her fingers along the underside of one of Sans’ ribs- the second most ticklish part of his body. She didn’t touch him. The hairs of her fingers hovered just above the bone surface, with just a whisper of air separating them. The almost-contact had an immediate, satisfying effect.

Sans writhed, snorting with laughter. The joyful sound was Toriel’s cue to begin tickling in earnest. Sans squirmed and dodged, but he couldn’t escape his relentless assailant and her expertly aimed fingertips. Her feather-light touches sent him into paroxysms of wanton merriment, and soon he was gasping for breath and begging her for mercy.

Her only response was an even more mischievous smile.

Sans gulped. She couldn’t have discovered his secret- his most ticklish spot, one guaranteed to have him contorting  and howling with laughter. She wouldn’t dare…! Toriel’s fingertips barely grazed his coccyx, and Sans screeched with mirth, nearly tumbling off of the bed from the extreme sensitivity of that particular bone.

The former Queen tickled Sans ruthlessly into exhaustion, then pulled him close to her chest to rest while he listened to the soothing beat of her SOUL. Contentment settled over Sans in the wake of the adrenaline from the tickle attack. He felt so calm.

The tired skeleton nestled his face into Toriel’s shoulder. Her sweet scent drifted into his nasal cavity once more, and he sighed happily. He could fall asleep so easily like this, with her warmth and that fresh clean smell of burning, and the smoke tickling at his sockets, and the… the smoke? The smell of burning?

“My quiche,” shouted Toriel, toppling Sans onto the floor as she leapt from the bed and ran to the kitchen.

The moment and the brunch were both ruined.


	27. Day Twenty-Six: FSG!Sans x UT!Papyrus x UF!Papyrus (Lactation, Roleplay, Toys)

**Summary for the Chapter:**

> Pairing: FSG!Sans x UT!Papyrus x UF!Papyrus
> 
> Featured Kinks: Lactation, Roleplay, Toys
> 
> Additional Warnings: Voyeurism, Fingering, Overstimulation, Masturbation, Sexual Exhaustion

“Does That  _Look_  Like An Udder To You?” snapped Edge when the Fellswap Sans, with his crisp uniform and commanding demeanor, affixed a cup from the breast pump to his cock as well as the large, perky breasts he’d summoned.

“I Told You To Summon Full Female Ecto. It’s Hardly My Fault That You Refuse To Listen,” responded the Sans, who preferred the moniker Wine, sharply. “You Should Be More Cooperative, Like Your Friend Here.” Wine patted Papyrus on his skull, and the much better behaved skeleton smiled and made an experimental moo sound to further immerse himself in his role.

It had been easy enough to get Papyrus to don the cowbell collar and cow ear-and-horn headband for their play session, but Edge had fought Wine’s instructions every single step of the way, complaining loudly about the accessories, the requested ecto-parts, and even the brand of sex toys scattered throughout the room. Wine wondered why Papyrus had brought his petulant friend along at all.

Once Wine finished hooking the other two skeletons up to the milking machine, he settled himself in his opulent armchair and poured himself a glass of his namesake, swirling the contents in his wine glass while his two little cows awaited his instructions.

“You’ll Be Riding Those Fucking Machines, Facing Me, Of Course, So I Suggest You Prepare Yourselves. I Won’t Go Easy On Either Of You.” Wine pointed with his half-filled glass to a pair of motorized fucking machines in front of him, set up with large studded dildos. The dildos already glistened with lube, but the sheer size of them meant that penetration would be difficult but extremely pleasurable.

With a lecherous grin, Edge pounced on Papyrus. Wine watched the scarred skeleton vigorously finger his friend. Papyrus’ back arched, and he pressed his soaking, aching pussy harder into Edge’s fingers. Arousal dribbled freely onto Edge’s hand.

Wine cleared his throat to remind Papyrus that foreplay was a two-way street if they were both going to enjoy the fucking machines. Fighting off the haze of lust that clouded his mind, Papyrus reached around, grabbing Edge’s ass cheeks and spreading them wide. Edge yelped when the first finger entered him, but he seemed to consider the mutual fingering to be some sort of competition.

Papyrus and Edge fingered each other at a feverish pace, gasping and moaning in mutual pleasure. Papyrus scissored his fingers inside of Edge’s asshole to stretch him out, and Edge added a third finger to Papyrus’ tight cunt, twisting and curling the digits inside of him. The two skeletons finally broke apart, ribcages heaving, and straddled their designated fucking machines.

Papyrus’ slick, eager pussy swallowed his sex toy with only minimal effort, but Edge struggled to fit his toy into his still painfully tight asshole. Once they were both seated, the pair of skeletons looked to Wine to get the machines started.

Wine idly stroked himself through his dress pants. He might even unfasten them to masturbate if the two skeletons at his disposal aroused him enough. Holding up the controls for the fucking machines, Wine asked his two toys if they were ready. Papyrus and Edge nodded, causing their cowbells to jingle. Instead of turning on the fucking machines, however, Wine pressed the ON switch for the breast pump.

“Surprise,” whispered the short skeleton with a devious sharp-toothed grin.

The breast cups suctioned onto Papyrus and Edge’s ecto-bodies, sealing with bruising force. The suction began immediately, pulling at the skeletons’ sensitive ecto-breasts and Edge’s thick, hard cock. Two pairs of nipples- one orange and one red- stood at attention, taut and straining before they finally gave and milk began to leak out of them into the collection cups.

Edge’s cock held out slightly longer, but the sucking force of the breast pump brought him to orgasm quickly enough. Edge stiffened, toes curling as cum spilled from his cock into a separate collection cup. The suction didn’t stop though. Edge’s cock stayed hard, and the pump milked him for every drop of cum his throbbing shaft could produce. Edge’s bones rattled from the strain of overstimulation already, and the fucking machines hadn’t even sputtered to life yet.

Wine unbuckled his belt and unzipped his pants, palming his cock. It was time for the real fun to start. His cows mewled so beautifully while the milk was being sucked from their breasts, and Wine couldn’t wait to hear their delirious cries when the dildos began savagely pounding their tight little fuckholes.

The fucking machines had three speeds- low, medium, and high. Wine considered the settings for only a brief moment before turning the dial from OFF directly to HIGH. Papyrus and Edge shrieked as the dildos hammered into their holes at a brutal pace. Eyelights rolled back into sockets, tongues lolled, and pelvises bounced up and down to the rhythm of the fucking machines’ thrusts. Fortunately each fucking machine had a bar installed at the front for the skeleton riding it to hold onto.

Sinking into the plush cushions around him, Wine watched the dildos utterly destroy his two pets. Setting aside his wine glass, he squeezed his cock with one hand and fondled the tip with the other. Soon, he was jerking himself off in earnest. Papyrus’ back arched into an almost impossible curve with his first orgasm. Wine grinned. The tall skeleton looked so beautiful when he came undone like this.  _Simply stunning._

The second orgasm caused Papyrus to squirt, and so did each orgasm after it until the base of the his fucking machine was coated in his juices and ever thrust made him scream for mercy. Edge came hard again and again, but eventually nothing more came out. The dry orgasms shook his frame until he went limp, losing consciousness from the overwhelming sensation. Papyrus slumped forward onto the handlebar of his machine soon after.

The two cowbells continued to jingle from the vibrations of the fucking machines’ engines.

Wine groaned in relief. reaching completion to the music of the bells. He shut off the breast pumps and fucking machines and closed his sockets to savor the bliss of his orgasm in silent darkness. Unfortunately, duty could not wait; his responsibilities prompted him to reopen his sockets.

Ignoring his two pets for the moment, Wine picked up the milk collection cups. Holding each one up to the light, he swirled the contents just as he had done with his wine.

The thick breast milk, infused with Papyrus and Edge’s magic, moved sluggishly in the containers, a perfect consistency to make whipped cream for his brother.


	28. Day Twenty-Seven: SpicyHoney (Voyeurism/Exhibitionism, Degradation, Against a Wall)

**Summary for the Chapter:**

> Pairing: UF!Papyrus x US!Papyrus (SpicyHoney)
> 
> Featured Kinks: Voyeurism/Exhibitionism, Degradation, Against a Wall
> 
> Additional Warnings: Possessiveness, Oral Sex, Fingering, Gaping, Creampie

“THE ONLY WAY YOU’LL SURVIVE IN THIS UNIVERSE IS IF THE OTHER MONSTERS HERE KNOW THAT YOU BELONG TO ME,” Edge growled against the side of Stretch’s skull.

“i get that, but there’s got to be a better way than this,” Stretch complained under his breath. Sure, Edge was sex incarnate when he got into one of his feral, possessive moods, but the two skeletons were standing outside… in Snowdin… surrounded by a crowd of Fellverse monsters with only a single row of Edge’s bone attacks to hold them back. “can’t you just bite me or something?”

A dark chuckle rumbled through Edge’s ribcage. “OH, I’LL BE DOING PLENTY OF THAT AS WELL.”

The imperious Captain of the Royal Guard grabbed a fistful of Stretch’s orange hoodie and yanked him forward to face the crowd. The red-tinted eyelights and fang-filled leers unsettled the gentle Underswap skeleton, but Edge pulled him away from the other monsters before they could lay so much as a claw on him.

“IN CASE ANY OF YOU FILTH WERE THINKING OF EARNING SOME EASY EXP, I JUST WANT TO REMIND YOU WHO THIS WEAK LITTLE SLUT BELONGS TO.”

Stretch sputtered, offended, but before he had a chance to form coherent words, Edge ripped his clothing into shreds. The denials died on his nonexistent lips. The second Edge’s sharpened phalanges scraped against his unmarked bones, the Underswap skeleton’s magic had formed, and arousal already dribbled from the silky slit to stain his thighs.

“YOU LOVE THIS, DON’T YOU? YOU WANT ME TO SPLIT YOUR CUNT OPEN WHILE THEY ALL WATCH! DISGUSTING!” sneered Edge. Stretch shivered in the cold air, yet he made no move to cover himself. Instead, he widened his stance, spreading his legs slightly. Tears pricked his sockets, and a hot blush glowed on his cheekbones. Yes, he did want it, and he hated that he wanted it.

“ON YOUR KNEES,” commanded Edge and Stretch instantly dropped into position, knees apart to show his pussy and asshole to the monsters milling behind the paltry barrier of bones. “CONVINCE ME THAT YOU DESERVE MY COCK.”

Puffs of warm breath condensed in the cold Snowdin air, giving away Stretch’s eager panting as he reached for Edge’s belt buckle. It didn’t matter; his palpitating pussy was on display, getting wetter and wetter with each passing second.

Edge’s belt buckle unfastened with a clink. His leather pants could barely contain his engorged cock, and when Stretch moved to unzip him, it forced the zipper open with its sheer size, bobbing free to slap Stretch in the face. Precum dribbled from the tip onto Stretch’s cheekbone like an icy kiss.

The thick crimson shaft was a sight to behold. As if the admirable length and superlative girth weren’t impressive enough, Edge’s cock boasted a row of sharp spurs lining the underside. The spurs would enter a partner smoothly, but after penetration, the backward-curved spikes dug in painfully and ravaged orifices from the inside out. Edge could control them… if he chose to.

An orange tongue circled the head of Edge’s cock, cleaning the precum from it before moving up and down the length of it, coating it in glistening saliva. Stretch kissed and gently suckled the barbs, imagining them dragging along his sensitive pussy walls. Closing his sockets and opening his mouth, Stretch took the huge shaft into his mouth, guiding it with his tongue until it hit the back of his throat. Much of Edge’s cock remained exposed, too large to fit in one mouthful.

“TAKE IT ALL, SLUT,” roared Edge, grabbing Stretch’s skull with both hands and slamming his cock all the way down into the other skeleton’s throat. Stretch gagged, unable to do anything more than convulsively swallow around the cock. Sucking or bobbing his head were out of the question because Edge held on tightly and facefucked him, not even allowing him a chance to breathe.

“CHOKE ON MY THICK COCK,” Edge moaned unnecessarily. Stretch couldn’t do anything else except choke with the barbed length slamming in and out of his throat at such a powerful and rapid pace. Edge closed his sockets in satisfaction and let his skull tilt back as bliss washed over him.

Tears streamed down Stretch’s cheeks, but he didn’t tap out as he and Edge had agreed upon earlier if things got too rough. Instead, he slipped two fingers into his wet, waiting pussy, scissoring them to show his fluttering holes and the sticky slick leaking down onto his thighs. He arched his back at the sound of the crowds mocking laughter, giving the citizens of Snowdin an even better view as he fingered his tight cunt desperately.

Edge’s sockets shot open when he felt Stretch’s moans vibrating through his cock. Was the Underswap skeleton masturbating during all of this? He  _was!_ _Unbelievable!_  Pausing his savage thrusting, Edge hauled Stretch up by the ribcage and spun him around to face the audience. With one hand, Edge supported Stretch’s ribcage; with the other, he lifted one of Stretch’s legs high, showing the lecherous crowd exactly what the lanky skeleton had been doing.

Stretch removed his fingers sheepishly, using the arousal-stained digits to spread his puffy pussy lips and show off his entrance from the new angle.

“DON’T STOP NOW,” said Edge in singsong mockery. “GET YOUR PUSSY LOOSENED UP FOR ME LIKE THE GOOD LITTLE WHORE YOU ARE, OR WOULD YOU RATHER I TEAR IT OPEN WITH MY COCK?”

“destroy me,” whimpered Stretch, just loud enough for the monsters at the front of the crowd to hear. They leaned forward in anticipation of what was to come, and the Royal Guard Captain did not disappoint.

Edge threw Stretch up against the wall of the abandoned Librarby, barely giving him an opportunity to brace himself before the dark crimson cock sank into his silky cunt. Stretch’s pussy stretched too far too fast, but moans of pleasure soon replaced his pained cries as his needy body adjusted. Though Edge kept his cock spurs softened while he pounded Stretch into oblivion, they still raked his tender insides and had his eyelights rolling back in his skull at the overwhelming sensation.

Stretch’s phalanges scraped helplessly at the brickwork of the Librarby wall as Edge used him, twisting his clit viciously and calling him a slut each time he spasmed and came, orgasming multiple times despite the rough treatment.

By the time Edge finished, cock emptied and finally tucked back into his clothing, Stretch lay sprawled at his feet in the snow. The Underswap skeleton was exhausted, and his pussy gaped wide open so that those gathered around could easily see the dark red cum oozing out of it each time it pulsed in aftershocks of intense pleasure.

Edge nudged Stretch’s prone form aside with one heeled boot, stepping up to the row of sharpened bone attacks separating him from the denizens of Underfell. “THIS SKELETON HERE SERVES AS MY PERSONAL LIVING FLESHLIGHT, AND I ASSURE ALL OF YOU WATCHING THAT HIS SLOPPY CUNT AND MEAGER EXP AREN’T WORTH THE UNENDING SUFFERING THAT WOULD BEFALL YOU FOR SCAVENGING MY LEFTOVERS.”

The observers dispersed; not a single one of them was willing to risk the Royal Guard Captain’s ire for a pussy that looked like it wouldn’t be closing up for weeks. Once the Town Square fell silent, deserted by all but the two skeletons, Edge scooped Stretch into his arms to carry him back to the house for some much needed aftercare.

“I BELIEVE I GOT THE POINT ACROSS,” chuckled Edge in a much softer tone than the one he’d used earlier.

“i dunno, Edge, some of those monsters looked pretty obstinate. maybe we should make this a weekly thing, eh?”

Edge quirked a bony eyebrow at his lover and smiled wickedly. It seemed that they had both enjoyed the experience more than they had intended.  _A weekly occurrence indeed…._


	29. Day Twenty-Eight: PuppyCherry (Omorashi, Stripping/Striptease, Humiliation)

**Summary for the Chapter:**

> Pairing: UF!Sans (Cherry) x SF!Papyrus (PuppyCherry)
> 
> Featured Kinks: Omorashi, Stripping/Striptease, Humiliation
> 
> Additional Warnings: Primal play (Predator/Prey), Biting, Knotting, Public Sex, Roleplay, Cum Inflation

Cherry had very little in common with the other monsters of the Underfell universe. The seasoned killers living in the Underground exuded an aura of menace that the small skeleton simply did not possess. While those around him boasted of high LV and superior battle patterns, his reluctance to fight and single HP left him with nothing but heaps of anxiety and a life of constant danger.

The house he shared with his brother in Snowdin offered Cherry a small modicum of comfort, however. Just a few steps from their back door laid a thickly shadowed forest where a timid, weak monster like Cherry could easily hide and find a few moments of blessed peace amongst the snow poffs. He seemed to be spending more and more time outdoors lately, escaping the troubles of his stressful life.

That morning, a rude phone call from Undyne had further soured his brother’s usually sour mood, and Papyrus yelled at him during breakfast. Convinced that he was nothing more than a weak, pathetic burden to his Royal Guard Captain brother, Cherry had run upstairs to hide his overflowing tears. If Papyrus saw him crying, he would probably mock Cherry’s unbecoming sensitivity.

Cherry needed to get away from the house to calm his nerves and collect himself. He selected an outfit from his closet that would look cute and fashionable on him, boosting his self-esteem, and he layered his undergarments for added protection from the Snowdin chill. A bustier with clips held his thigh-high stockings in place underneath soft leather boots. A lacy petticoat added volume to his loosely pleated skirt.

The small skeleton fastened a scarlet hooded cloak over his peasant top and tossed some snacks and a blanket in a picnic basket in case he got hungry while he was out. His brother always demanded that he carry a dagger to protect himself, but Cherry could never bring himself to stab someone. He left the weapons to his tough-as-nails brother and tucked a romance novel that he’d found at the Dump into his basket instead.

Raising his hood to cover his skull, Cherry strolled down the snow-strewn path into the shadowy Snowdin Forest. He traveled away from the areas where the Snowdin Royal Guard patrolled and towards the Ruins where few other monsters bothered to visit. He wanted to be alone, but though he saw no other monsters, a second, darker shadow stalked his from the cover of the underbrush.

Something felt off to Cherry, and his nerves blazed with warnings that he brushed off as anxiety symptoms. There were no other monsters out here. He would’ve seen them. He would’ve heard them. He would’ve… with a soft  _oof!_ Cherry collided with something very large and very solid. He hoped it was just a slightly squishy rock, but in his SOUL he knew it wasn’t.

Gulping nervously, Cherry looked up ( _and up and up!_ ) into a pair of blazing dark orange eyelights set in the sockets of a gold-fanged face. Clouds of hot breath blasted his face as the large skeleton monster looming over him huffed and puffed, inhaling the scent of his fear sweat.

“m-my what b-big eyes you have,” stammered Cherry dropping his picnic basket and backing away from the dangerous-looking skeleton.

“all the better to see defenseless little skeletons such as yourself wander foolishly into my woods,” replied the fanged skeleton, prowling forward in pursuit. He licked his gold fang, smiling wolfishly at Cherry, and his careful bootsteps made no sound on the hard-packed snow of the path.

“and what a v-very long t-t-tongue you have,” whimpered Cherry, bumping into a tree that prevented him from backing up any further. He was trapped!

“all the better to eat you with.” the tall skeleton closed the distance between himself and Cherry in a single long stride.

He breathed his words right against Cherry’s neck, using two long phalanges to push aside the red cloth of the hood. Cherry could feel the other skeleton’s erection through the layers of fabric separating them. He couldn’t even manage to squeak out another observation, so the taller monster spoke again.

“and in case you were wondering, the big cock is for filling your tight little pussy with my cum,” he chuckled in his deep, gruff voice. His warm damp tongue swiped up the side of Cherry’s neck, leaving a trail of saliva to cool in the frigid air. “now take off your pretty clothes so i don’t have to rip them.”

Cherry finally found his voice. “please, Mr. Wolf, have mercy.”

“i won’t ask again.” The “wolf” grabbed Cherry and shoved him into the center of the trail. “now strip!”

Trembling with fright, Cherry regretted the large amount of orange juice he’d consumed during breakfast. He had to pee, and his fear of the wolf made holding it extremely difficult. Squeezing his thighs together in an attempt to ease the pressure, Cherry unfastened and removed his cloak, folding it carefully before setting it on the ground.

The wolf circled Cherry as he lifted his blouse over his head and placed it atop the folded cloak. Next, the small skeleton slid his skirt and petticoat to the ground. The wolf’s hungry stare intensified, and Cherry clenched his teeth against the urge to wet himself.

“please stop staring,” begged Cherry. If he removed any more clothing, the lanky skeleton would see his lewd parts! He’d already seen the bulge in the wolf’s tastefully faded blue jeans; what would happen if he revealed his body to the beast?

Cherry’s fingers shook so badly that he could barely unclip his stockings. The hooks holding his bustier closed presented even more of a delay. The undergarment finally dropped to the snow, and Cherry’s hands shot up to cover his exposed breasts. The cold air blasted his sensitive nipples, and they hardened instantly behind his hands.

“don’t look,” Cherry cried, embarrassed, but his embarrassment quickly turned to horror. His bladder protested the combination of fear and bone-chilling temperature, and he couldn’t stop the flow of urine any longer. Piss gushed out of him, soaking through his panties and running in rivulets down his thighs to melt the snow at his feet. Cherry blushed. The release of the tension felt so good even though the act of wetting himself only added to his distress.

The wolf pounced, slashing through Cherry’s steaming, pee-soaked panties with one sharpened phalange. Ignoring the urine, the tall skeleton rubbed his hands along Cherry’s warm, wet slit, pushing aside his pussy lips to circle his entrance with eager fingers.

“no, don’t touch there. it’s dirty!” wailed Cherry, more humiliated than he’d ever been in his entire life. He stood naked in the forest, covered in his own piss, with a big, bad wolf fingering him. Worse, when the wolf withdrew his fingers and dropped his pants, Cherry could imagine the thick, hard cock penetrating him, stretching him, filling him, and his body ached for it.

The wolf sank his fangs into Cherry’s neck, the pointed tips of the teeth pressing into the spaces between Cherry’s vertebrae. The sensation was both terrifying and exhilarating; this powerful monster could dust him in the space of a breath. Steadying himself, the wolf forced his cock slowly into Cherry’s tight cunt, inch by throbbing, agonizing inch.  Cherry moaned and mewled, but he didn’t struggle. It felt so good that the pleasure overwhelmed him.

Cherry soon found himself on all fours on the forest path being pounded by the massive skeleton. He never expected the knot to fit into his tiny pelvic inlet, but the wolf snapped his hips and Cherry’s pussy suddenly expanded then closed around the knot. He could feel both cock and knot throbbing inside of him, and his worries melted away as ecstasy tingled like an electric current through his bones.

A different kind of pressure built in the small skeleton’s abdomen. His pussy clamped down around the wolf’s cock, and they came together. Cherry squirted then fell limp and spent in the wolf’s arms while the larger skeleton emptied his seed, cock pulsing, into Cherry’s willing body. The sheer volume of the wolf’s cum caused Cherry’s stomach to swell, but he held all of it, much to the wolf’s surprise and delight.

Picking up Cherry’s clothing, both clean and soiled, the wolf carried him to a more secluded spot in the forest. Curling protectively around the smaller skeleton, the wolf fished around in the basket for a towel to clean him off.

“feelin’ better?” asked the wolf, draping a blanket over both of them.

“mm-hmm,” murmured Cherry, tucking himself against the wolf’s ribcage.

“i didn’t go too far this time?”

“nuh-uh,” responded Cherry drowsily.

This was the best part of their Little Red Riding Hood roleplay sessions- falling asleep in his big bad wolf’s loving embrace, all tuckered out and relaxed from a thorough fucking.


	30. Day Twenty-Nine: HoneyKetchup (Glory hole, Double (or more) Penetration, Sleepy Sex)

**Summary for the Chapter:**

> Pairing: UT!Sans x US!Papyrus (StonerBros, HoneyKetchup, LazyBoners), Classic fontcest, Swapcest, Kedgeup, multiple pairings
> 
> Featured Kinks: Glory hole, Double (or more) Penetration, Sleepy Sex
> 
> Additional Warnings: Sex Work/Prostitution, Bathroom Sex, Gaping, Creampie, Swallowing, Socket Sex, Slight Cum Inflation, Voyeurism
> 
> Note: This chapter includes skeletons from Undertale, Underswap, Underfell, and Swapfell engaging in sex with Classic Sans and Swap Paps.

The first mistake was leaving Sans and Stretch to clean up after the party. The second, and arguably worst mistake, was trusting them to actually do chores without a responsible monster to supervise them. Of course the pair of lazybones opted to sprawl out on the sofa instead of cleaning. What did those other skeletons expect from the Co-Champions of Laziness?

Sans and his Underswap cohort flipped through channels on the TV in a tangle of floppy limbs and drowsy, half-lidded sockets. Nothing on the television really appealed to the two skeletons more than the prospect of a co-op couch nap, so Stretch switched the TV off and let the remote fall to the floor.

Lifting his head from the soft sweatshirt material of Stretch’s hoodie, Sans glared at the lightswitch. The bright illumination of the overhead light cast a definite shadow over any potential sleep-related activities. In the spirit of laziness, he had installed a Clapper, meaning that he could shut off the lights with a mere clap of his hands. Somehow though, he could not muster the energy to elevate both hands and bring them together quickly enough to produce sound. The action required way too much effort.

It wouldn’t be the first time that he slept with the lights on.

Stretch settled into a more comfortable position on the couch, and Sans adjusted himself as well. Unfortunately, all of the wiggling and movement in order to achieve optimum napping positions ended up causing their pelvises to rub together. Both skeletons froze, staring at the glow of magic forming in each of their shorts.

“i’ll be  _up_  all night at this rate,” joked Stretch tiredly.

Sans yawned. “now y’know i’m against any form of  _hurrying_ , but… may i suggest a  _quickie_?” He started to waggle his bony brows, but gave up when the gesture further exhausted him.

Stretch eyed the smaller skeleton up and down, forming an idea for sexual satisfaction with minimal exertion. “roll onto your stomach. you can leave your shorts on.” Sans rolled onto his stomach without protest. He could hear Stretch unbuttoning and unzipping his khaki cargo shorts in the background. Stretch didn’t even bother removing the article of clothing; he just pulled his cock out with his shorts still on as well.

Pushing aside the loose fabric of Sans’ basketball shorts, Stretch could easily see that Sans had summoned a plush and glistening pussy. Perfect. Stretch laid down carefully on top of Sans, situating his cock between Sans’ pussy lips. He rocked his hips slowly, rutting against Sans’ silky slit until arousal dribbled from Sans’ pussy onto his cock. Sans closed his sockets, making soft, contented noises.

“ready?” murmured Stretch against the side of his partner’s skull. His cock slipped and slid in Sans’ juices, catching several times on his pussy opening. It would be so easy to enter him from this angle….

“mmhmm,” Sans mumbled. Stretch’s cock was hard, thick, and warm. Sans couldn’t wait to be filled up and fucked to sleep, especially since it didn’t require him to do any work.

Stretch used his hands to spread Sans’ pussy lips; his cock penetrated Sans’ tight little hole with little resistance because the smaller skeleton was so relaxed. Stretch grunted at the sensation of slick, tight walls squeezing around his shaft, and Sans let out a quiet mewl of surprise at how full and stretched out he felt. The two sleepy skeletons fit together well.

Their joining didn’t involve passion and desperation. It was characterized more by slow, deliberate movements and affectionate touches. Stretch’s languorous thrusts rocked Sans’ smaller frame in a calming rhythm, and Stretch paused each time he hilted so that he and Sans could indulge in the pleasure together.

The sex wasn’t a frantic scramble for release either. The easygoing skeletons only wanted a bit of relief from the heightened urges of their pelvises brushing. Sans had several small orgasms that set his pussy fluttering around Stretch’s cock, and when Stretch eventually came, only a few hot strands of cum escaped him.

Satisfied by taking the edge off, the pair of satiated skeletons dozed off together with Stretch’s erection slowly going lax inside of Sans until their magic eventually dissipated, leaving a small sticky mess on the fabric of the couch.

* * *

“UNBELIEVABLE! THOSE LAZY SHITS DIDN’T CLEAN A FUCKING THING!”

“AND THEY MADE EVEN MORE OF A MESS ON THE COUCH! THOSE STAINS ARE HARD TO REMOVE!”

“you would know, eh, Blue?”

“DON’T BE DISGUSTING, BROTHER, OR YOU’LL BE CLEANING IT UP YOURSELF.”

“that’s not fair! i helped make food and decorate! they were supposed to clean!”

“THAT IS TRUE, RED. WE HAD AN AGREEMENT, AND THEY BROKE IT. I THINK A PUNISHMENT WOULD BE APPROPRIATE IN THIS CASE.”

“DO YOU HAVE SOMETHING IN MIND?”

“I DO, ACTUALLY, AND IT INVOLVES ALL OF OUR PARTY GUESTS, ESPECIALLY THE ONES FROM THE UNDERLUST UNIVERSE…”

* * *

Papyrus lifted his brother gently from the couch; Edge slung Stretch carelessly over his shoulder. Neither of the sleeping skeletons awoke while being handled. Blue stared in utter shock, but Red barely noticed as he tapped away on his phone, sending out a mass invite to their friends explaining the fun they could soon be having in Underlust.

”I CAN’T BELIEVE THEY SLEPT THROUGH OUR CONVERSATION  _AND_ BEING PICKED UP!” Blue poked his brother’s sneaker-clad foot for emphasis, and the appendage swung limply.

“nothing wakes up a Sans-type when he’s having a good nap, especially not his loud brother,” the stocky Underfell skeleton commented with a snort. Turning to his own brother and Papyrus, he gave them a curt nod. “the Lust bros are up for it. i can teleport us directly to the basement of their Grillby’s club, and the others will meet us there.”

“THANK YOU, RED,” said Papyrus with genuine gratitude.

“you can thank me by letting me have my turn in the first round,” quipped Red, stepping close to the other skeletons for a group teleport.

* * *

Groggy groans announced Sans and Stretch’s gradual return to consciousness. The two skeletons blinked their bleary sockets and slowly absorbed their new surroundings. The soft couch cushions upon which they had fallen asleep were gone, replaced by a model of a human public restroom stall, complete with fake toilet. Numerous holes adorned the walls at various heights.

“Ah, our guests are awake. Now we may begin.” A pleasant voice spoke over a hidden loudspeaker in response to the two skeletons’ confused expressions. “Welcome to Grillby’s Bar and Strip Club, and thank you for agreeing to participate in this Two-Skeleton Glory Hole Event.”

“glory hole?” mouthed Stretch, but Sans’ eyelights were focused on a familiar and delectable orange ecto-cock pushing through one of the holes at mouth level.

“when in Rome,” said Sans with a shrug, opening his mouth and summoning a tongue to guide the cock inside with.

“we’re not in Rome, we’re in the Lustverse,” grumbled Stretch to nobody in particular. Sans was busy positioning himself so that a spiked red cock sliding through another hole could tease his pussy while he sucked off what was presumably- from the color and Sans’ eagerness- his brother’s cock.

Stretch sighed. “when in the Lustverse, i guess…” The sticky sensation of precum dribbled onto his naked pelvis, and he quickly formed his own ecto-parts to pleasure it. He’d recognize that soft blue glow and impressive girth anywhere. Maybe if they serviced the other skeletons long enough, they would be forgiven for falling asleep instead of cleaning up after the party.

Sans and Stretch accepted cock after cock, working themselves into a frenzy of lust and pleasure. At one point, Sans had even pressed his eye socket to one of the holes and allowed a massive dark orange shaft to socket-fuck him and cum into his skull. Pussies and assholes gaped and leaked multi-colored cum onto the floor, and both Sans and Stretch’s stomachs swelled with how much magic they had swallowed.

Without a word passing between them, they agreed to keep going until their debt to their brothers was paid in full or they collapsed from exhaustion.

* * *

Papyrus tapped out after four satisfying rounds, surrendering his spot at the glory holes to the Sans from Swapfell. Blue took a much-needed breather on one of the tastefully arranged sofas in the waiting area, watching the other skeletons have their fun on the video monitors with Papyrus, and Edge prepared to get back into the rotation once Red finished his current session.

The Papyrus from Underlust approached the three hosts, quietly relaying a message to them from Grillby. It seemed that the Snowdin Royal Guards from Underlust were willing to pay handsomely to join in the festivities… if Sans and Stretch could handle their knots, that is.

Papyrus, Edge, and Blue exchanged looks. Blue and Edge nodded for Papyrus to speak on their behalf.

“THE MORE THE MERRIER,” declared Papyrus.

“hey Boss, can this be my punishment next time i don’t do my chores?” asked Red, pulling his saliva-coated cock away from the hole in the wall. He didn’t know whose mouth he’d used, and he didn’t care. The skeleton who serviced him had worked his throat and tongue like a pro, drinking down every drop of his cum when he orgasmed.

“THE MORE THE MERRIER,” said the Underlust Papyrus with a wink.


	31. Day Thirty: Mythtale Swapfellcest (Stockings/Tights/Pantyhose, Breast Worship)

**Summary for the Chapter:**

> Pairing: Mythtale SF!Sans x Mythtale SF!Papyrus (Mythtale Swapfellcest)
> 
> Featured Kinks: Stockings/Tights/Pantyhose, Breast Worship
> 
> Additional Warnings: Fontcest/Swapfellcest, Masochism, Biting, Nipple Piercings
> 
> Note: These specific characterizations belong to mythtale.tumblr.com

“do you need some assistance in there, m’Lord?” Slim asked through the thick oak door to his Lord’s bedroom. The vampire and his demon master had just returned from shopping, and Black had immediately scurried away to his chambers to don some clothing items he’d purchased.

He still had yet to emerge.

“N-NO! I’M FINE,” snapped Black, trying several different poses and checking his reflection in his full-length mirror. He wanted to look perfect when he called his servant into the room. Unfortunately, he had a very obvious problem.

Black had purchased a pair of expensive hose after seeing the way that the filthy kitsune Stretch ogled his faerie lover’s behind in a similar article of clothing. The hose that the faerie wore showed off his posterior superbly, contouring the curves and giving just the right amount of lift. Black had commissioned a pair last week to his unique specifications, and after collecting them today, tried them on to find that they had a similar effect on his own hindquarters.

The problem arose when Black faced his mirror head on. Each tiny movement he made caused the clinging fabric to rub against his cock, and now he had an erection outlined clearly in the fabric! Precum beaded through the material itself, causing a dark wet spot to add to the issue! The tunic he selected to showcase his ass offered no reprieve for his plight.

No matter how much Black tugged at his shirt, he couldn’t cover his erection. Even worse, every attempt only increased the friction on his cock, causing his face to flush with arousal. The situation certainly wasn’t improving with the passage of time, so Black shuffled to the door to let his servant in, trying not to rub himself too much in the process.

Slim rushed into the room, concerned about his Lord’s well-being. He noticed the difference in Black’s usual garb right away before his eyelights drifted downwards to see the demon’s cock straining against the hose, leaking precum as the fabric squeezed it. Black crossed his legs in an attempt to hide it, but his desire scented the air with pheromones that the vampire couldn’t ignore.

“m’Lord, you smell… good enough… to eat,” purred Slim, closing in on the demon and resting one hand lightly over his throbbing cock. Unable to resist, Black ground his erection against his servant’s hand, completely forgetting that his original intent had been to bring attention to his ass.

“DEVOUR ME THEN,” ordered Black, and his servant obediently swept him up into his arms and carried him to the canopied bed. Slim settled Black into his lap, stroking his Lord’s cock through the hose without removing them. The texture of the fabric provided additional stimulation for the demon’s already aching shaft, but he needed relief…  _NOW_!

Slim didn’t utter a word; he simply sank his gold fang into his Lord’s clavicle from behind. The demon’s rich purple magic seeped from the wound and filled his mouth with the delicious essence of his master. His own magic gathered low in his pelvis, but he ignored it, concentrating on feeding and on pleasuring his beloved Lord. The music of Black’s ragged, desperate breathing and the flavor of his magic on the vampire’s tongue and sliding down his throat provided all of the satisfaction that he needed.

Black moaned. He loved the pain and the tugging sensation of magic being drained from him to feed his loyal servant. He loved being the sole source of sustenance for Slim, making the vampire rely on him for the very thing he required to survive. He frequently told himself that Slim only stayed with him for the ready source of magic though he knew in his SOUL that their complex relationship went much deeper than dependence for nourishment.

The vampire’s hand returning to his cock jolted Black from his musings. Slim ran his hand along the length of his Lord’s cock hard and fast, until the friction and heat had Black writhing and screeching in agonizing bliss in his servant’s lap. The demon was close- so close that it hurt.

Shredding the fabric of the hose with his sharp phalanges, Slim gripped Black’s cock tightly and began to pump it, squeezing and sliding his hand along the length with ruthless speed and focus. Lifting his Lord easily, he flipped the demon onto his hands and knees on the bed, rutting against his round, luscious ass while he jerked the demon off.

Screaming in pure ecstasy, Black came into his servant’s hand. Thick ropes of hot cum shot from his cock onto Slim, the ruined hose, and the bedding. Slim didn’t stop when his Lord orgasmed though. He milked every drop of cum from Black’s cock before lifting his hand to his mouth to taste it. Delicious.

Black laid on the bed, panting, sockets closed as he rode out the orgasm. Slim stood to fetch warm water and towels to clean his Lord up, but Black laid a hand on his arm to stop him.

“THOSE HOSE WEREN’T THE ONLY ITEM I PICKED UP TODAY,” Black teased, lifting his shirt to show two custom made nipple clips that he had found at a jeweler’s shop during their shopping excursion earlier. A set of silvery fangs framed each of Black’s nipples, the tips digging lightly into the delicate flesh of his breasts.

“for me?” Slim asked, surprised and flattered. They were perfect, and it was obvious that his Lord had chosen them with certain  _ideas_  in mind. Slim stared, imagining the sensation of the smooth metal on his tongue while he licked and suckled his Lord’s nipples.

“DO YOU LIKE THEM?” prompted Black, unnerved by his servant’s silence. Maybe he had misjudged the-

Slim pounced like a predator going in for the kill, straddling the demon and pinning him to the bed. His mouth descended on one of his Lord’s tender nipples while his hands busily massaged his master’s breasts. His answer was made obvious by his groans of pleasure and the gentle, reflexive humping motion of his hips.

The vampire clearly remembered the first time that his Lord had revealed these beautiful breasts to him. Black was so nervous! As if Slim would ever reject him for something so lovely as a body with both a cock and soft, feminine breasts! Slim took every opportunity to give Black’s tits special attention to set the demon’s mind at ease, and it appeared that Black was rewarding his efforts with these oh-so-inviting vampire-themed nipple clips.

The tips of the fangs dragged against the sensitive flesh of Black’s nipple with each powerful suckle. Slim rolled the nipple of the other breast between his thumb and forefinger, tugging it until it too scraped the sharp metal. The demon craved pain during sex, and Slim indulged him, applying his own fangs to the nipple in his mouth. He pawed his Lord’s breasts roughly, growling with frenzied lust.

Black mewled and arched his back, pressing his body against his servant’s, eyelights rolling back as pleasure overwhelmed him. Slim loved his Master’s expression when he came completely undone like this.

“mmm, m’Lord… so good.” Slim nuzzled and nipped Black’s tits, leaving small marks all over them and making Black scream and fist the sheets as his body went rigid.

“SERVANT… I… I’M… AAAHHH!” Black came again, spilling more of his seed onto himself and his servant. This time he allowed Slim to clean him off properly, but the vampire no longer had any desire to use warm water or towels on his Lord’s delectable body. Instead, he licked the demon’s cum from his own body and his master’s, treating himself to a dessert like no other.

Eventually he left his Lord’s side to change the bedclothes and fetch pajamas for a very exhausted but well-satisfied Black.

The vampire tucked his demon master under the fresh blankets, crawling into bed with him only once his duties were completed. Under the guise of unconscious movement, Black snuggled up against his servant, and Slim rested his chin atop his Lord’s skull, nibbling one of the demon’s horns as he drifted off to sleep.

Black never told Slim that he loved him, and Slim never asked him to. Somehow, though, without the words ever passing between them, the sentiment was understood.


	32. Day Thirty-One: Dreamcest (Bondage, Tentacles, Double (or More) Penetration, Cum Inflation, Breeding)

**Summary for the Chapter:**

> Pairing: Dream x Nightmare (Dreamcest)
> 
> Featured Kinks: Bondage, Tentacles, Double (or More) Penetration, Cum Inflation, Breeding
> 
> Additional Notes: Fontcest/Dreamcest, CONTAINS NONCON

_How had things turned out so wrong?_

It only took one incautious step for Dream to fall victim to one of his brother’s traps. Now, the embodiment of goodness and positivity found himself dangling upside down from an oozing tentacle that sprang from the writhing darkness and negativity that his brother had become. Dream had let his guard down, and now he would pay the price. He closed his sockets, bracing himself for pain.

Nightmare savored his long-awaited victory. He’d finally captured the goody-goody who ruined his life so long ago. Now that he held Dream in his clutches, Nightmare had time to reminisce on the reason for his revenge. The reason for his exile. The reason for his current, sludge seeping form.

They had been close brothers who shared a sacred duty- guarding a magical tree and the fruits it once bore. They shared a destiny, yet Dream stole all of the glory and left his brother with nothing but the people’s scorn. Dream still wore the crown of his office, but Nightmare’s had long since melted away courtesy of Nightmare’s dripping toxins.

Dream and Nightmare could never go back to those days. The tree was gone, and they themselves had changed drastically… and soon Dream would be dead.

Nightmare held Dream suspended in the air with a single tentacle wrapped around his ankle, ready for the fatal strike. The golden brother whimpered and struggled, but he could never break Nightmare’s grip. Glaring at his brother, Nightmare seethed with his remembered jealousy and rage, yet as the moment of Dream’s destruction neared, Nightmare wondered if he truly wanted to kill his brother-nemesis and eradicate the final apple from the tree they’d once protected… together.

_Together._  A strange sensation rose in Nightmare’s chest. Could it be… nostalgia? Did he truly miss his brother and the closeness they had once shared? Ridiculous! And yet…

“Are you going to kill me,” Dream asked softly, trying to put on a brave face.

A slow smile spread through the viscous black matter of Nightmare’s face. “No, dear brother, I’m not going to kill you… I’m going to breed you. We’ll be a family again, but this time you’ll stay with me forever.” Nightmare laughed maniacally as Dream attempted once more to squirm free of the tentacles now crawling across his body.

One thick, oozing tentacle slid up Dream’s pant leg while another curled around his neck from behind and slipped down the collar of his shirt, Flexing, the appendages tore Dream’s clothing apart, leaving him hanging, exposed, in front of Nightmare’s deranged eyes. Dream pled for mercy, but Nightmare ignored him, concentrating instead on the golden magic reluctantly pooling in his helpless brother’s pelvis.

“Your mouth says no, but at least your body is honest,” chuckled Nightmare, throwing his brother onto the ground. Dream never even had a chance to regain his footing before the invasive black tentacles swarmed him once more.

Nightmare showed neither restraint nor mercy, plunging multiple thick tentacles into every available orifice of Dream’s body, stretching his asshole and cunt to the breaking point until the inky tendrils writhed in the bulging ectoflesh of his stomach. Nightmare sent his magic into his brother’s throat last. He wanted to hear his brother’s desperate screeching before he silenced Dream with a thick knot of his substitute cocks.

Dream felt like his brother’s tentacle were splitting him in half. He was sure his magic was tearing, but he couldn’t move much less stop Nightmare. When his dripping mess of a brother starts to pump the tentacles in and out of him, Dream nearly passed out, body going rigid then limp and eyelights rolling back in his skull. The intense pain was more than he could bear, but he had no outlet for his pain with tentacles face-fucking him and holding his body motionless.

Somehow though, pleasure managed to pierce the excruciating miamsa in his mind. His nerves burned with pain but they also tingled with pleasure. The fullness that threatened to burst his magic also brought him close to climax. How could this be happening? Why did it feel so  _good_  to be violated like this by his own brother?

Nightmare chuckled darkly. “Are you actually enjoying this, brother? I can feel your tight little cunt clenching around me and your juices flowing down my tentacles. How filthy of you.”

As much as Nightmare would love to continue tormenting his brother, an ache spread from his abdomen to his tentacles. He was close to cumming, and he needed to make sure that he was deep inside of his brother’s pussy when he did. Breeding Dream would take every drop of hot sticky cum he could produce.

The tentacles pounding into Dream’s ass and throat released their meager loads before Nightmare retracted them, relieving some of the pressure in Nightmare’s magic. Much to the oozing monster’s surprise, Dream came, squirting his fluids onto the remaining tentacles inside of his trembling pussy when Nightmare’s hot cum filled his ass and mouth.

Dream gagged and attempted to swallow the thick, sticky offering, but when the tentacles withdrew from his ass and mouth, he coughed, sending the cum pouring out of the now-vacant holes to run down his femurs and chin.

“Breed me, brother,” mewled Dream, dazed and twitching with cum still dribbling from the corner of his mouth.

“Oh, I will,” taunted Nightmare. “Over and over and over again.” With each word he spoke, the mass of tentacles slammed into Dream’s pussy with savage force. For the grand finale of his climax, Nightmare used his tentacles to spread Dream’s pussy impossibly wide from the inside out. Tears streamed down Dream’s cheeks as the twin sensations of pleasure and pain overwhelmed him, blurring his vision so that he couldn’t see what Nightmare had planned.

A massive tentacle, larger than all of the tentacles still inside of Dream’s pussy combined, sprang from Nightmare’s pelvis. Dream screamed and begged as Nightmare shoved the over-sized tentacle into his raw pussy one torturous inch at a time. Nightmare closed his sockets, reveling in the music of Dream’s cries which had merged into a feverish chant of “breed me” being uttered over and over in a frantic, sobbing babble.

Nightmare couldn’t hold back for a second longer. With a low moan of carnal bliss, Nightmare tensed, and the huge tentacle began to pulse, pouring bucketful after bucketful of thick, potent cum directly into his brother’s womb. Dream’s magic bulged to accommodate the copious amounts of cum spilling from his brother’s tentacle cock.

Dream fainted from the overstimulation, and Nightmare himself nearly blacked out from the huge magic transfer. Grabbing his brother by the neck, Nightmare teleported them to his bedroom to recuperate in safety.

Nightmare stared down at his golden brother, so small and fragile, laying naked on his bed with cum streaming from his asshole and cunt as his spasming body emptied of the excess that it couldn’t hold. How the hell was Dream supposed to get pregnant with all of the cum overflowing from his pussy and soaking into the blankets?! Nightmare sighed. He’d just have to keep breeding Dream until something stuck.

Nightmare’s perpetual frown faded at the thought of Dream’s stomach swollen with their future children instead of his inky dark magic. Nightmare got into the bed next to Dream, who promptly rolled over and snuggled up to him. Sighing, Nightmare rested a hesitant hand on his brother’s shoulder. Dream smiled in his sleep.

_How had things turned out so well?_

 

**Notes for the Chapter:**

> There will be TWO bonus chapters!  
> One will be a Horrortale Sans and Lust Sans drabble and the other will be a continuation of Day Twenty (Chapter 21).


	33. BONUS: Classic Fontcest (Continuation of Day Twenty/Chapter 21)

**Summary for the Chapter:**

> Pairing: UT!Papyrus x UT!Sans (Classic fontcest)
> 
> Featured Kinks: Dominance, Begging
> 
> Additional Warnings: Fontcest, Light Bondage, Object Insertion, Facial

Papyrus trained extensively with Blackberry and his brother Mutt for weeks. He perfected each domination technique with ease, eager to try them out on his own brother. Now he stood in front of the door to the home that he and his brother Sans shared in Snowdin taking deep, even breaths and steeling himself for their first impromptu session.

Papyrus would finally establish himself as the dominant partner, and Sans would learn his place whether he liked it or not. Thanks to his special training, Papyrus would make sure that he liked it, craved it, begged for it. Tightening his grip on the handle of the kit that he and Blackberry had painstakingly assembled, Papyrus opened the door.

Predictably, Sans sprawled across the sofa, one slipper sliding off of one foot, clothes unwashed, and a trail of ketchup stains and chip crumbs forming a wayward trail from his chest to the couch cushions to the floor. The sight strengthened Papyrus’ resolve. He set down the case holding the tools of domination, rested his hands on his hips, and waited for Sans to notice and acknowledge his arrival.

“hey, baby bro,” said Sans, flopping over onto his stomach, sending the slipper plummeting to the floor and food detritus flying. Papyrus hated being called baby bro, and Sans knew it. “what’s  _poppin’_?” Sans somehow managed to pop every single joint in his body with minimum effort or movement, throwing his brother a sideways glance and a shit-eating grin to gauge his reaction, but Papyrus’ sockets were already trained elsewhere.

Sans had one job, one single task that Papyrus had asked him to do for the entire day. It wasn’t difficult; it wasn’t time-consuming. Papyrus just wanted Sans to pick up the damn sock on the floor and put it in the laundry basket, mere feet away. The sock’s continued presence in its crumpled heap on the floor incensed him. He unlatched the case, and the lid flipped open, blocking the contents from Sans’ nonchalant but somehow still observant eyelights.

“I TOLD YOU TO PICK UP YOUR SOCK SANS.” Papyrus spoke in a low, serious voice, hands trailing over various implements that he could use on his brother.

“i did,” Sans responded cheekily. His left eyelight flashed with magic, and a blue haze surrounded the sock. It lifted slightly off of the floor before falling back to its original place. Sans laughed.

_Infuriating_ , thought Papyrus.  _Unacceptable._  His gloved hand closed around a riding crop, the perfect tool for the job.

Tucking the riding crop close to his body to keep it hidden, Papyrus stepped forward. “LET’S GET YOU OUT OF THOSE FILTHY CLOTHES, SANS,” he purred dangerously, grabbing one leg of Sans’ shorts and roughly yanking them off, knocking the other slipper off of his brother’s foot. It hit the floor with a thump, followed a moment later by the softer sound of basketball shorts pooling on carpet.

Sans’ hands quickly covered his bare pelvis, but they couldn’t completely hide the excited rush of magic beginning to gather there, casting a faint blue glow on his pale white bones. “whoa, what the heck, Paps? this isn’t like you!”

Without missing a beat, Papyrus tugged Sans’ hoodie up over his head, using the momentum of the motion to pull Sans’ small frame flush with his own. Tossing the hoodie aside, Papyrus finished stripping his brother by pulling the front hem of his shirt over his head and twisting it expertly around his wrists, effectively securing Sans’ arms behind his back. The smaller skeleton still refused to take the situation seriously.

“geez, bro, if i didn’t know better, i’d think you had a  _bone_  to pick with me.”

Papyrus responded with a sigh and a shake of his head. He shoved Sans hard into the back of the couch, prying his femurs apart and putting a luscious blue pussy on prominent display. Interesting. Sans had formed a pussy without any instructions from Papyrus. That saved some time... something Papyrus wasn’t entirely sure he approved of.

The riding crop slid between Sans’ plump pussy lips, parting them enough for Papyrus to see his inner folds glistening with arousal. Sans panted softly as the stiff handle of the riding crop rubbed his dribbling slit. The smaller skeleton relaxed his guard, always willing to do absolutely nothing while someone else did all of the work for him.  _Perfect._

“I THINK IT’S ABOUT TIME WE ESTABLISH WHO’S IN CHARGE AROUND HERE, BROTHER.” Sans attempted to interrupt, probably with a pun or quip, but Papyrus talked over him. “YOU CAN START BY CALLING ME MASTER.”

On the final word, Papyrus flicked the riding crop, snapping the leather end of it against Sans’ clit sharply. The sudden assault to his sensitive nub made Sans screech and arch his back. Finally he understood that Papyrus meant business; finally he was paying attention.

Papyrus stepped back, ready to begin an exercise designed to teach Sans to address him properly. Sans wiggled, missing the attention of the riding crop, desire sending aching jolts through his bones.

“don’t stop,” whimpered Sans. The plea was a promising start, but his brother had forgotten one important thing.

Papyrus lifted one foot and nudged his brother’s fluttering opening with the toe of his boot. Fresh arousal streaked the polished red leather, and Sans gritted his teeth at the tortuous teasing. “YOU FORGOT SOMETHING,” prompted the taller skeleton, twisting his boot to dig into his brother’s tender ectoflesh.

“master,” Sans cried obediently, too desperate to be obnoxious.

Papyrus withdrew his boot. “SAY IT PROPERLY.”

Indecision played across Sans’ features. His desire to give his younger brother a hard time warred with the maddening, consuming lust that would be satiated if he just uttered a few placating, deferential words.

The comedian in Sans did not allow him to pass up a golden opportunity, regardless of the consequences.

“y’know, i’m a master too,” Sans said slyly, hurrying to deliver his joke before Papyrus could silence him, “a  _master baiter!_ ” The stocky skeleton cackled as his brother’s eyes bulged.

The pun was impressive, but Papyrus refused to admit it. Instead, he twirled the riding crop in one gloved hand before unceremoniously shoving it, handle first, into Sans’ waiting pussy. The action wiped the ever-present smile off of Sans’ face in an instant, replacing it with an open mouth and lolling tongue. Sans’ eyelights rolled back, and he moaned beautifully- music to Papyrus’ nonexistent ears.

The walls of Sans’ greedy pussy clamped down on the slim handle of the riding crop. The initial penetration set off an explosion of pleasure deep inside of him, but it quickly faded. Papyrus didn’t work the crop in and out of him or move it at all in fact. He just left it there. Despite the tightness of Sans’ cunt, the handle didn’t fill him like he needed it to in order to relieve the ache between his femurs. Without the delicious stretch of a larger object or the friction of motion, the insertion only heightened Sans’ sensitivity.

Sans whimpered and writhed. Everything within him screamed for stimulation- something, anything- and soon he screamed aloud as well, surrendering to his brother’s will in hopes of garnering even the slightest erotic touch to tame the burning hunger in his pussy.

“please bro- i mean, Master. please, Master, i’m sorry. please just touch me,” Sans begged, huge tears gathering in his sockets before overflowing onto his cheekbones and running down his face.

The sight of Sans, desperate and begging- crying even- awoke Papyrus’ erection with near painful efficiency. His magic gathered fast into a huge, hard shaft, but Sans had not earned the sweet release that Papyrus’ cock could afford him. Patience would prove to be an effective weapon in dominating his brother.

Papyrus hooked the waistband of his hotpants with a thumb and tugged them down, exposing himself to Sans in all of his thick, glowing, pre-cum dripping glory, and the smaller skeleton actually salivated at the sight, opening his mouth wider and extending his tongue invitingly.

“I DON’T THINK YOU REALLY DESERVE THIS.” Papyrus stroked his cock slowly, spreading the precum all along the length until his cock glistened with it, throbbing as yet another bubble of orange-tinted fluid gathered at the tip. Sans strained to catch it with the tip of his tongue.

Papyrus knelt on the couch, straddling his brother. His cock hovered just above Sans’ face, tantalizingly close. Sans babbled a litany of pleas for his brother to close that final distance and face fuck him, socket fuck him, just fuck him!

Sensing his brother’s frenzied thoughts, Papyrus remained calm, stoic, stone still and completely in control of the entire situation. “ASK ME FOR IT PROPERLY,” he instructed Sans coolly, continuing to stroke himself right above Sans’ uplifted face. He could imagine thrusting his full length down his brother’s warm, wet throat and the way it would feel as Sans choked and gagged around his cock. Not that Papyrus would give him what he wanted; he needed to put Sans in his place, after all.

“please Master,” wailed Sans, squirming and striving to capture the heat of Papyrus’ throbbing cock with his mouth. “please let me suck your cock, Master. face fuck me, Master. use me, destroy me, make me your little cum slut. please, Master, i’ll do anything!”

Growing nearly delirious with the strength of his need, the sound of Sans’ voice drove Papyrus as he jerked his cock fast and hard. Each supplication made his shaft swell with his rapidly approaching orgasm. Papyrus could feel the tension gathering as his hand moved- up down, up down- with increasing speed. He concentrated on the rare treat of Sans’ sobbing, gasping, no-longer-smiling face and came.

Thick strands of bright orange cum shot from Papyrus’ cock to spatter  haphazardly across his brother’s face, coating his cheeks and dripping into one eye socket. Grabbing his brother’s skull in both gloved hands, Papyrus crammed his cock into Sans’ mouth, emptying the rest of his load deep in his brother’s throat. The smaller skeleton’s tongue pressed the underside of his pulsating cock, milking every last drop of cum from him.

“SWALLOW,” Papyrus commanded, feeling the sensation of his brother’s throat tightening around him seconds later. “GOOD BOY.” Papyrus released Sans’ skull, letting his still rock-hard cock bob free of his mouth.

Orange cum covered Sans’ face. Papyrus admired his handiwork; it was a good look on his brother. Humming thoughtfully, the tall skeleton considered giving Sans a real reward and himself the satisfaction of sinking his length into his brother’s tight, soaking pussy.

One matter required his attention first though.

Papyrus stepped back off of the couch and pulled the handle of the riding crop out of Sans’ pussy. The smaller skeleton’s juices coated it thickly, and Papyrus raised it to his nasal cavity, inhaling deeply and taking in the heady scent of his brother’s arousal. Sans cried out at the sudden emptiness inside of him, but his hopeful eyelights never left the glowing orange ecto-flesh standing at attention right in front of his face.

Reaching behind his brother, Papyrus untwisted the fabric holding his wrists together. Honestly, Sans could have easily freed his own hands and used his fingers to pleasure his pussy and relieve himself. Curiosity and laziness in equal measures prevented Sans from acting. He wanted to see what Papyrus would do, how far he would go, and whether or not he would enjoy it.

The tall skeleton tipped his brother forward onto his hands and knees on the floor. “YOUR SOCK,” Papyrus intoned icily, “IF YOU WANT YOUR REWARD, GO PICK IT UP.” Papyrus’ cock twitched when he said reward, making it clear exactly what the reward entailed.

* * *

Sans crawled towards the delinquent garment. He grabbed it and turned towards the laundry hamper, lifting it up to drop it inside with the rest of the dirty clothing that he and his brother generated… then he paused.

Blue-tinted arousal stained his femurs as it dribbled out of him. His pussy quivered and ached for a thorough fucking, but something about this new domineering side of Papyrus really turned him on. Maybe he wasn’t quite ready for a reward yet.

Maybe he’d get some more punishment first.

Sans let the sock fall from his hand back onto the floor.


	34. BONUS #2: BloodLust (Marking, Body Worship, Breeding)

**Summary for the Chapter:**

> Pairing: HT!Sans (redtomatofan version) x UL!Sans (BloodLust)
> 
> Featured Kinks: Mild Marking, Mild Body Worship, Breeding
> 
> Additional Warnings: Exhibitionism, Gaping, Creampie, Mild Cum Inflation

_This place has potential_ , thought the skeleton monster with purple heart-shaped eyelights. Monsters in his universe simply called him Lust, a moniker earned through his inexorable charms and ability to seduce literally anyone. Legend had it that he had once seduced a moss-covered rock though the rock could not confirm or deny it.

Lust strolled casually through the barren Snowdin Forest, hands tucked into the pockets of his purple, blue-fur-lined vest. This definitely appeared to be the kind of universe where monsters fought and struggled just to survive, the kind of place that would yield strong breeding stock… if only he could find any monsters living here. Lust’s sky blue boots crunched the snow in the absolute silence as he wandered further into the forest of dead and dying trees. He never even noticed the glowing red eyes tracking him from the shadows.

A stocky skeleton monster with a jagged hole in his skull watched the newcomer with grim concern. The brightly colored clothing on the other skeleton stood out like a beacon in the harsh white snow and charred black background of trees. This flamboyant skeleton didn’t belong in a dying world. Not that it mattered- the ravenous monsters of the Horror-verse would find him soon enough and mar his pristine bones as they tore him apart for any iota of sustenance they could glean.

The injured skeleton stepped forward with a sigh. He couldn’t let the carefree skeleton be killed just for wandering into the wrong universe. Sugar would expect better of him, and he never let his brother down if he could help it.

Sensing eyes on him, Lust whirled just in time to see a broad-framed skeleton monster with a gaping head wound reaching for him. He leapt backwards, startled by the skeleton’s appearance and stealthy approach.

“heh, don’tcha know how t’greet a new friend?” the skeleton rumbled in a deep voice that sent shivers up Lust’s spine. Lust’s heart-shaped eyelights roved over the other skeleton’s body, assessing him for breeding potential. He could almost smell the virility pouring off of this intimidating monster. He wondered if a quick blowjob counted as an appropriate “greeting.”

“i’m Lust, but you can call me yours,” Lust offered, ignoring the other skeleton’s outstretched hand in favor of stepping in close and pressing himself against the slightly shorter but much broader skeleton. The skeleton with the skull injury sidled away, making Lust pout, but he kind of enjoyed a monster that played hard to get. The chase sweetened the conquest.

“name’s Blood, and you seem to be lost, pal. this universe ain’t safe for visitors,” warned Blood. “ya don’t look like ya’ve seen what a lifetime of starvation n’ violence does to monsters. better leave b’fore someone less friendly finds ya.”

“such savagery,” exclaimed Lust, though he sounded more aroused than shocked or frightened, “but i came here because my universe has its own problems. monsters are dying out, and we can’t reproduce.”

“well y’ain’t gonna find any babies ‘round here.”

“i’m not looking for babies. i’m looking for strong monsters that are capable of breeding. monsters like you. i think we could help each other, Blood.” Lust slunk close to the other skeleton yet again, brushing their ribcages together and giving Blood a half-lidded stare of seduction. Blood seemed skeptical, so Lust whispered his idea straight into the other skeleton’s ear canal:

“all the food you can dream of can be yours, and all you have to do to earn it is fuck. We can give it a test run right here and now if you’d like.” Lust groped the front of Blood’s unwashed basketball shorts, and sure enough, he found the other skeleton’s magic tingling in his pelvis, ready to form into ecto-flesh at any moment.

“i got a brother,” Blood said reluctantly. He could never accept such a gracious offer without bringing Sugar along to share in the spoils. If they needed a breeder, he’d do it. He’d do anything to feed himself and Sugar.

“he’d come with us, obviously. every Sans needs his Papyrus!” Lust practically salivated on himself. His prize was so close he could almost taste it, and oh how he wanted to taste it.

“not for breedin’ though-” Blood quickly corrected, but Lust waved his words aside with a sultry smile.

“of course not. only willing monsters become breeders. besides, it’s really you i’m after. those strong bones, crisscrossed with scars yet still graceful in their curvature. you’re a magnificent creature, Blood, and i want you to be mine.”

Lust’s eagerness and overt sexuality fanned a flame in Blood’s core that he hadn’t even known was still there. It nearly overwhelmed his constant gnawing hunger… but not quite. He agreed to collect his brother and travel back to Lust’s universe with him. A hot meal and a hot pussy sounded like a dream come true, and Blood wasn’t willing to let this opportunity slip away while he weighed the abundant pros and nonexistent cons.

Lust told Blood that their arrangement would be discussed later, after he settled in, so Blood and his brother, Sugar, spent their first few weeks in Lust’s universe eating, resting, and recuperating their magic. Once Blood finally got used to having his fill of food, however, a new appetite awakened in him. The ambient sexual nature of the Lust-verse saturated the air, and Blood breathed it in eagerly. Soon, he found himself seeking out Lust’s company.

“Blood!” Lust greeted him, “are you enjoying yourself?”

“ya promised food in exchange for fuckin’. ya held up yer end of the bargain, so i guess it’s time to get down ta business,” Blood’s bright red eyelights raked Lust’s purple ecto-flesh like a pair of greedy, wandering hands.

“so eager,” sighed Lust, fanning himself though it did nothing to tame his excitement. “i hope you don’t mind an audience though. the other monsters here are anxious to see you… perform.”

“let ‘em watch.” Blood’s voice came out husky, and Lust knew he’d chosen a winner. He gave Blood instructions to meet him backstage at Grillby’s Club. The fire elemental always had live entertainment in his establishment, but tonight the entire future of their universe would hang in the balance as monsters watched their own beloved Lust fuck a potentially fertile monster from another universe.

Blood felt the weight of their expectant eyes on him the moment he stepped onto the platform, wearing only his now-clean shorts. Muscles rippled along his deep red ecto-body, magic he couldn’t have kept summoned like this back when he couldn’t remember what an actual meal tasted like. All of his thoughts promptly melted into an incoherent puddle when Lust took the stage alongside him.

Lust wore nothing except a flimsy black silk robe that clung in all of the right places on his toned body. He moved with feline grace, circling Blood before closing the distance between them to slide his hands down Blood’s chest and abs. Lust moaned as his phalanges explored the hard muscles.

“stunning,” he purred so that only Blood could hear, prowling around to stare at the view from the back. Lust ran his hands over Blood’s back, following the curve of his spine down to his ass, which he grabbed and squeezed with both hands. “lovely,” he whispered, almost to himself.

When Lust finished his appraisal of Blood, he stood in front of him and slowly let the fabric of his robe slip off of his shoulders. Blood’s hands assisted it in falling away completely until it drifted gracefully to the floor. Blood leaned in and captured Lust’s mouth in a rough kiss; Lust braced himself against Blood’s ample pecs and gently pushed him away. He would be setting the pace this evening.

Lust’s kissed and licked his way along Blood’s jawline until his mouth and tongue found the stocky skeleton’s cervical vertebrae. Lust nipped and teased at the bones of Blood’s neck, kissing the base of his throat between his collarbones then sucking gently on one of the clavicles. Blood moaned, content to let Lust have his way for now. Lust nipped and sucked at Blood’s neck and collarbones until dark marks appeared, a sign that Blood had been claimed.

Chuckling at his handiwork, Lust continued to kiss his way down Blood’s body, occasionally giving a nip or gentle suckle to the dark crimson ecto-flesh, leaving a trail of hickeys in his wake as he made his way down to the waistband of Blood’s pants. Breathing heavily in anticipation of the main event, Lust slipped his phalanges underneath the waistband and slowly, languorously tugged the shorts down, baring Blood’s pelvis to the crowd.

Lust blinked in surprise as Blood’s thick erection bobbed free of the basketball shorts and came to rest against his cheekbone, spilling sticky beads of viscous precum onto Lust’s face. A indistinguishable murmur swept through the crowd, but Lust didn’t miss a beat. Turning his head, he caught the tip of Blood’s cock with his tongue, sweeping the rest of the precum into his mouth before tilting his face upwards to address Blood.

“i think there’s been a misunderstanding,” said Lust, standing up and facing Blood. “ _you’re_  not here to breed  _me_.  _i’m_  going to breed  _you_.” Blood’s eyes dropped to Lust’s pelvis where the other skeleton’s twitching cock stood at enthusiastic attention.

Blood had assumed that Lust had summoned a pussy, and he’d been too mesmerized by Lust’s provocative movements and sensuous facial expressions to check. Still, he swore he’d do anything to keep Sugar here where they could be safe and well-fed, and he stood by that vow. Dismissing his cock, Blood focused on re-forming his magic into a plump, slick pussy that looked good enough to eat. Lust apparently agreed because he lowered himself again, licking his mouth, heart-shaped eyelights locked on Blood’s decadent, glistening folds.

Lust couldn’t wait to fill Blood up with his cum again and again, as often as Blood could safely handle, as often as it took until a soulling swelled that sexy blood-red abdomen.

* * *

Lust held Blood aloft with his hands under the broad skeleton’s thick thighs which were bruised and tender from the slamming of Lust’s insistent hips. Using two of his phalanges, Lust spread the other skeleton’s pussy lips, putting his gaping cunt on display for the cheering crowd. Purple cum poured out of Blood’s pussy, dripping in thick globs onto the stage. Blood’s stomach swelled with the volume of the cum still inside of him, but Lust made a _tsk_ -ing sound.

“oh no,” Lust cried in mock concern, “it just keeps flowing back out! i guess we’ll have to keep going then!”

The throbbing shaft filled Blood’s raw, aching pussy again. The crowd cheered louder. Blood kept telling himself that he was doing this for himself and for Sugar, that it was all worth it, that eventually Lust’s stamina would run out and he would empty himself at last.

It took hours.

And it was only their first session.


End file.
